Journal Pre-proof
4
2
.2.9
8-(1-hydroxy-3-methylbutyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione (12i): This compound was prepared
-
1
according to the GP. yield 85%; white solid; m.p. 106-108˚C; R
f
= 0.50 (4% MeOH/Chloroform); FT-IR (neat, cm ): 3389, 2959,
933, 2872, 1699, 1649, 1544, 1439, 1218, 1037, 975, 746; H NMR (400 MHz, CDCl ) δ = 4.83 (m, 1H), 3.97 (s, 3H), 3.49 (s,
H), 3.35 (s, 3H), 3.24 (br, 1H), 1.87-1.78 (m, 2H), 1.64-1.56 (m, 1H), 0.95 (d, J = 6.4 Hz, 6H); C NMR (100 MHz, CDCl
55.51, 155.07, 151.69, 147.44, 107.95, 65.21, 44.93, 32.22, 29.64, 28.04, 24.56, 23.27, 21.89; HRMS (ESI) Calculated for
1
2
3
1
C
3
1
3
3
) δ
+
13
H
20
N
4
O
3
[M+H] : 281.1608, Found : 281.1609.
2
.2.10 8-(1-hydroxy-2-methylpropyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione (12j): This compound was prepared
-
1
according to the GP. Yield 90%; white solid; m.p. 194-196 ˚C; R
f
= 0.40 (4% MeOH/Chloroform); FT-IR (neat, cm ): 3431, 2956,
924, 2871, 1694, 1641, 1544, 1433, 1217, 1033, 971, 742; H NMR (400 MHz, CDCl ) δ = 4.45 (t, J = 6.5 Hz, 1H), 3.97 (s, 3H),
.51 (s, 3H), 3.36 (s, 3H), 3.05 (br, 1H), 2.14 (m, 1H), 1.04 (d, J = 6.7 Hz, 3H), 0.87 (d, J = 6.8 Hz, 3H); C NMR (100 MHz,
CDCl ) δ = 155.51, 154.55, 151.68, 147.52, 107.84, 72.11, 34.14, 32.35, 29.86, 28.04, 18.91, 17.96; HRMS (ESI) Calculated for
1
2
3
3
1
3
3
+
C
12
H
18
N
4
O
3
[M+H] : 267.1452, Found : 267.1455.
2
.2.11 8-(1-hydroxycyclohexyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione (12k): This compound was prepared
-
1
according to the GP. Yield 71%; white solid; m.p. 216-218 ˚C; R
f
= 0.55 (4% MeOH/Chloroform); FT-IR (neat, cm ): 3439,
933, 2851, 1688, 1642, 1536, 1427, 1217, 972, 743, 523; H NMR (400 MHz, CDCl ) δ = 4.12 (s, 3H), 3.45 (s, 3H), 3.31 (s, 3H),
) δ = 157.44, 155.48, 151.73, 146.78, 108.24,
1
2
3
1
3
3
.03 (br, 1H), 2.01-1.89 (m, 4H), 1.72-1.62 (m, 6H); C NMR (100 MHz, CDCl
3
+
72.06, 36.39, 34.16, 29.73, 28.04, 25.20, 21.44; HRMS (ESI) Calculated for C14
H
20
N
4
O
3
[M+H] : 293.1608, Found : 293.1607.
2
.2.12 8-(1-hydroxycyclopentyl)-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione (12l): This compound was prepared
-
1
according to the GP. Yield 73%; white solid; m.p. 182-184 ˚C; R
f
= 0.5 (4% MeOH/Chloroform); FT-IR (neat, cm ): 3440, 2938,
859, 1680, 1641, 1533, 1425, 1215, 972, 743, 523; H NMR (400 MHz, CDCl ) δ = 4.06 (s, 3H), 3.41 (s, 3H), 3.33 (s, 3H), 2.26
m, 2H), 2.11-2.05 (m, 2H), 1.92-1.89 (m, 2H), 1.79-1.71 (m, 2H); C NMR (100 MHz, CDCl ) δ = 156.95, 155.45, 151.60,
46.57, 108.36, 79.97, 39.54, 33.60, 29.68, 28.10, 23.89; HRMS (ESI) Calculated for C13
79.1455.
1
2
(
1
2
3
1
3
3
+
18 4 3
H N O [M+H] : 279.1452, Found :
2
.2.13 8-(hydroxymethyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione (13a): This compoundwas prepared according to the
-
1
GP. Yield 65%; white solid; decompose at 280 ˚C; R
f
= 0.40 (10% MeOH/Chloroform); FT-IR (neat, cm ): 3237, 3154, 3018,
1
2960, 2831, 1681, 1546, 1420, 1217, 1027, 869, 814, 670, 537; H NMR (400 MHz, DMSO) δ = 11.05 (s, 1H) 5.58 (t, J = 5.8
1
3
Hz, 1H), 4.52 (d, J = 5.8 Hz, 2H), 3.83 (s, 3H), 3.28 (s, 3H); C NMR (100 MHz,) δ = 155.53, 153.14, 151.39, 149.03, 108.04,
+
55.79, 32.28, 28.91; HRMS (ESI) Calculated for C
8 10 4 3
H N O [M+H] : 211.0826, Found : 211.0827.
2
.2.14 8-(1-hydroxyethyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione(13b): This compound was preparedaccordingto the
-
1
GP. Yield 68%; white solid; m.p. 250-254 ˚C; R
f
= 0.525 (10% MeOH/Chloroform); FT-IR (neat, cm ): 3527, 3332, 3149, 3021,
1
2828, 1678, 1547, 1421, 1297, 1218, 1156, 1105, 1035, 870, 752, 672, 546, 454; H NMR (400 MHz, DMSO) δ 11.02 (s, 1H),
1
3
5
.59 (d, J = 5.8 Hz, 1H), 4.86 (p, J = 6.4 Hz, 1H), 3.87 (s, 3H), 3.29 (s, 3H), 1.44 (d, J = 6.6 Hz, 3H); C NMR (100 MHz,
+
DMSO) δ 155.70, 155.59, 151.40, 148.90, 107.88, 61.59, 32.33, 28.92, 21.70; HRMS (ESI) Calculated for C
9
H
12
N
4
O
3
[M+H] :
225.2273, Found : 225.2275.
2
.2.15 3,7-dimethyl-8-(tetrahydrofuran-2-yl)-3,7-dihydro-1H-purine-2,6-dione (13c): This compound was preparedaccording
-
1
to the GP. Yield 54%; white solid; m.p. 236-238 ˚C; R = 0.70 (10% MeOH/Chloroform); FT-IR (neat, cm ): 3154, 3029, 2828,
f
1
1680, 1545, 1414, 1340, 1217, 1043, 861, 752, 544, 465; H NMR (400 MHz, CDCl
3
) δ 8.34 (s, 1H), 5.02 (t, J = 6.9 Hz, 1H), 4.02
(
s, 3H), 3.94 (dt, J = 15.6, 7.8 Hz, 2H), 3.52 (s, 3H), 2.62 – 2.52 (m, 1H), 2.33 – 2.25 (m, 1H), 2.21 – 2.12 (m, 1H), 2.09 – 2.00
1
3
(m, 1H); C NMR (101 MHz, CDCl
3
) δ 154.81, 153.11, 151.06, 149.39, 108.67, 72.69, 69.06, 32.45, 29.72, 29.07, 26.03; HRMS
+
(ESI) Calculated for C11 [M+H] : 251.1139, Found : 251.1141.
14 4 3
H N O
2
.2.16 8-(1-hydroxyethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione(14a):This compound wasprepared accordingto the
-1
GP. Yield 41%; white solid; m.p. 190-192 ˚C; R
f
= 0.375 (10% MeOH/Chloroform); FT-IR (neat, cm ): 3413, 3252, 2980, 1700,
1
1
638, 1554, 1504, 1366, 1218, 1163, 1106, 1057, 988, 748, 500; H NMR (400 MHz, DMSO) δ 5.59 (d, J = 4.9 Hz, 1H), 4.73 (dt,
1
3
J = 11.8, 5.9 Hz, 1H), 3.38 (s, 3H), 3.18 (s, 3H), 1.38 (s, 3H); C NMR (100 MHz, DMSO) δ 157.71, 154.65, 151.73, 148.28,
+
106.61, 63.53, 30.21, 28.23, 22.91; HRMS (ESI) Calculated for C
9 12 4 3
H N O [M+H] : 225.0982, Found : 2250983.
2
.2.17 1,3-dimethyl-8-(tetrahydrofuran-2-yl)-3,7-dihydro-1H-purine-2,6-dione (14b): This compoundwas prepared according
-
1
to the GP. Yield 45%; white solid; m.p. 228-230 ˚C; R
707, 1635, 1549, 1489, 1405, 1351, 1219, 1062, 986, 739, 504; H NMR (400 MHz, CDCl
.8 Hz, 1H), 4.12 (dd, J = 13.7, 7.6 Hz, 1H), 3.97 (dd, J = 15.0, 7.2 Hz, 1H), 3.61 (s, 3H), 3.47 (s, 3H), 2.45 (tt, J = 15.0, 7.6 Hz,
f
= 0.714 (4% MeOH/Chloroform); FT-IR (neat, cm ): 3206, 2944, 2882,
1
1
5
3
) δ 11.79 (s, 1H), 5.14 (dd, J = 7.6,
1
3
1
H), 2.30 – 2.19 (m, 1H), 2.12 – 1.94 (m, 2H); C NMR (101 MHz, CDCl
3
) δ = 155.67, 155.44, 151.77, 149.26, 106.65, 74.93,
+
69.41, 32.21, 30.23, 28.38, 25.75; HRMS (ESI) Calculated for C11 [M+H] : 251.1139, Found : 251.1137.
14 4 3
H N O
2
.2.18 8-acetyl-1,3,7-trimethyl-3,7-dihydro-1H-purine-2,6-dione (16): Dissolved the 8-(1-hydroxyethyl)-1,3,7-trimethyl-3,7-
dihydro-1H-purine-2,6-dione(50mg) in TBHP (1mL) and heated thereactionmixture at 100 ˚C for overnight.The usual work-up
procedure followed by column chromatographyfurnishedthe desired pure product. Yield 96%; solid; m.p. 182-184 ˚C; R = 0.857
f
-
1
(
6
4% MeOH/Chloroform); FT-IR (neat, cm ): 2957, 1766, 1685, 1653, 1594, 1542, 1460, 1414, 1369, 1231, 1185, 1033, 968, 742,
1
13
56, 530, 412; H NMR (400 MHz, CDCl
3
) δ = 4.33 (s, 1H), 3.61 (s, 1H), 3.43 (s, 1H), 2.71 (s, 1H); C NMR (100 MHz, CDCl
3
)