1334
V. Masevicius et al.
PAPER
3
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 38.9, 45.4, 97.2, 114.2,
130.89, 130.94, 132.1, 132.9, 135.0, 137.5, 140.2, 158.8, 167.1,
168.2.
1H NMR (300 MHz, DMSO-d6): δ = 0.77 [d, J = 6.8 Hz, 6 H,
3
CH(CH3)2], 1.23 [d, J = 6.8 Hz, 6 H, CH(CH3)2], 2.45 (s, 3 H,
SCH3), 2.95–3.07 [m, 2 H, 2 × CH(CH3)2], 3.34 (s, 3 H, SO2CH3),
4.76 (s, 2 H, CH2), 7.09 (s, 1 H, CH), 7.16–7.35 (m, 3 H, Ar-H), 7.36
(br s, 2 H, NH2).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 24.5, 25.2, 28.7, 40.6,
45.0, 97.4, 113.5, 125.3, 130.0, 132.0, 141.1, 149.9, 158.7, 167.1,
168.2.
Anal. Calcd for C15H14Cl2N4O3S2: C, 41.58; H, 3.26; N, 12.93.
Found: C, 41.51; H, 3.23; N, 12.86.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(3,4,5-trimethoxyphenyl)methanesulfonamide (5f)
Yield: 170 mg (79%); white solid; mp 226.5–228.5 °C (MeCN).
IR (KBr): 3426, 3120 cm–1 (NH).
1H NMR (300 MHz, DMSO-d6): δ = 2.44 (s, 3 H, SCH3), 3.20 (s, 3
H, SO2CH3), 3.64 (s, 3 H, OCH3), 3.73 (s, 6 H, 2 × OCH3), 4.97 (s,
2 H, CH2), 6.66 (s, 2 H, Ar-H), 7.18 (br s, 2 H, NH2), 7.56 (s, 1 H,
CH).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 37.0, 45.2, 56.8, 60.7,
96.9, 106.9, 115.3, 134.4, 137.8, 139.7, 153.4, 158.7, 167.1, 168.2.
Anal. Calcd for C21H28N4O3S2: C, 56.22; H, 6.29. Found: C, 56.09;
H, 6.34.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
4-nitro-N-phenylbenzenesulfonamide (6a)
Yield: 182 mg (82%); yellowish solid; mp 274.5–276 °C (DMF–
H2O).
IR (KBr): 3444, 3370, 3346 (NH), 1530, 1350 cm–1 (NO2).
1H NMR (300 MHz, DMSO-d6): δ = 2.44 (s, 3 H, SCH3), 4.96 (s, 2
H, CH2), 7.00–7.09 (m, 2 H, Ar-H), 7.25–7.35 (m, 3 H, Ar-H), 7.39
(s, 1 H, CH), 7.60 (br s, 2 H, NH2), 7.97 (d, 3J = 8.7 Hz, 2 H, Ar-H),
8.49 (d, 3J = 8.7 Hz, 2 H, Ar-H).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 45.6, 96.7, 114.6, 125.5,
129.0, 129.3, 129.9, 130.1, 137.6, 139.9, 142.3, 151.0, 158.7, 167.3,
168.2.
Anal. Calcd for C18H22N4O6S2: C, 47.56; H, 4.88. Found: C, 47.94;
H, 4.95.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(2-nitrophenyl)methanesulfonamide (5g)
Yield: 140 mg (72%); yellow solid; mp 233–235 °C (n-BuOH).
IR (KBr): 3411, 3159 (NH); 1531, 1340 cm–1 (NO2).
1H NMR (300 MHz, DMSO-d6): δ = 2.45 (s, 3 H, SCH3), 3.24 (s, 3
H, SO2CH3), 5.05 (br s, 2 H, CH2), 7.10 (br s, 2 H, NH2), 7.44 (s, 1
H, CH), 7.56–7.65 (m, 1 H, Ar-H), 7.76–7.85 (m, 2 H, Ar-H), 7.96
(d, 3J = 7.2 Hz, 1 H, Ar-H).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 37.8, 44.8, 97.4, 114.1,
126.0, 130.0, 130.3, 131.4, 134.5, 140.3, 149.7, 159.0, 167.0, 168.1.
Anal. Calcd for C20H17N5O5S2: C, 50.95; H, 3.63; N, 14.85. Found:
C, 50.84; H, 3.51; N, 14.60.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(2,5-dimethoxyphenyl)-4-nitrobenzenesulfonamide (6b)
Yield: 210 mg (83%); yellow solid; mp 248.5–250 °C (toluene).
IR (KBr): 3446, 3370, 3306 (NH), 1530, 1350 cm–1 (NO2).
1H NMR (300 MHz, DMSO-d6): δ = 2.45 (s, 3 H, SCH3), 3.26 (s, 3
H, OCH3), 3.59 (s, 3 H, OCH3), 4.89 (br s, 2 H, CH2), 6.55–6.57 (m,
1 H, Ar-H), 6.87–6.90 (m, 2 H, Ar-H), 7.19 (br s, 2 H, NH2), 7.40
(s, 1 H, CH), 8.04 (d, 3J = 8.9 Hz, 2 H, Ar-H), 8.46 (d, 3J = 8.9 Hz,
2 H, Ar-H).
Anal. Calcd for C15H15N5O5S2: C, 44.00; H, 3.69; N, 17.10. Found:
C, 44.11; H, 3.67; N, 17.11.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(naphthalen-1-yl)methanesulfonamide (5h)
Yield: 90 mg (46%); white solid; mp 200.5–201.5 °C (i-PrOH).
IR (KBr): 3453, 3362 cm–1 (NH).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 44.8, 55.9, 56.1, 97.0,
113.6, 114.7, 115.6, 118.4, 125.1, 125.5, 129.9, 140.0, 144.4, 150.7,
151.2, 153.1, 158.9, 167.2, 168.2.
1H NMR (300 MHz, DMSO-d6): δ = 2.41 (s, 3 H, SCH3), 3.34 (s, 3
H, SO2CH3), 4.90 (d, 2J = 15.3 Hz, 1 H, CHaHb), 5.73 (d, 2J = 15.3
Hz, 1 H, CHaHb), 7.19–7.70 (br s, 2 H, NH2), 7.22 (s, 1 H, CH),
7.28–7.36 (m, 1 H, Ar-H), 7.41–7.48 (m, 1 H, Ar-H), 7.56–7.64 (m,
1 H, Ar-H), 7.85–7.97 (m, 3 H, Ar-H), 8.01–8.06 (m, 1 H, Ar-H).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 37.1, 46.7, 97.1, 114.5,
124.1, 125.9, 126.4, 126.9, 127.1, 128.4, 129.6, 133.7, 134.5, 135.9,
139.8, 158.6, 167.1, 168.0.
Anal. Calcd for C22H21N5O7S2: C, 49.71; H, 3.98. Found: C, 50.00;
H, 3.94.
N-(4-Acetylphenyl)-N-({4-amino-2-(methylthio)furo[2,3-d]py-
rimidin-5-yl}methyl)-4-nitrobenzenesulfonamide (6c)
Yield: 187 mg (78%); yellowish solid; mp 289–290.5 °C (MeCN).
IR (KBr): 3480, 3446, 3384 (NH), 1528, 1352 cm–1 (NO2).
Anal. Calcd for C19H18N4O3S2: C, 55.05; H, 4.38; N, 13.52. Found:
C, 54.97; H, 4.28; N, 13.30.
1H NMR (300 MHz, DMSO-d6): δ = 2.43 (s, 3 H, SCH3), 2.55 (s, 3
H, COCH3), 5.01 (s, 2 H, CH2), 7.00–7.60 (br s, 2 H, NH2), 7.27 (d,
3J = 8.7 Hz, 2 H, Ar-H), 7.42 (s, 1 H, CH), 7.89 (d, 3J = 8.7 Hz, 2 H,
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(biphenyl-4-yl)methanesulfonamide (5i)
Yield: 130 mg (62%); white solid; mp 258.5–260.5 °C (MeCN).
3
3
Ar-H), 8.00 (d, J = 9.0 Hz, 2 H, Ar-H), 8.50 (d, J = 9.0 Hz, 2 H,
Ar-H).
IR (KBr): 3462, 3416, 3364 cm–1 (NH).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 27.5, 45.2, 96.6, 114.3,
125.6, 129.0, 129.8, 130.1, 136.9, 140.1, 141.6, 142.0, 151.1, 158.6,
167.4, 168.2, 197.8.
1H NMR (300 MHz, DMSO-d6): δ = 2.44 (s, 3 H, SCH3), 3.22 (s, 3
H, SO2CH3), 5.02 (s, 2 H, CH2), 7.23 (br s, 2 H, NH2), 7.34–7.49 (m,
5 H, Ar-H), 7.50 (s, 1 H, CH), 7.62–7.69 (m, 4 H, Ar-H).
13C NMR (75 MHz, DMSO-d6): δ = 14.0, 37.0, 45.1, 96.8, 115.3,
127.4, 128.0, 128.5, 129.4, 129.7, 137.9, 139.66, 139.68, 140.4,
158.7, 167.3, 168.3.
Anal. Calcd for C22H19N5O6S2: C, 51.45; H, 3.73. Found: C, 51.88;
H, 4.14.
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(4-chlorophenyl)-4-nitrobenzenesulfonamide (6d)
Yield: 177 mg (74%); beige solid; mp 273 °C (dec.) (MeCN).
IR (KBr): 3434, 3384 (NH2), 1526, 1349 cm–1 (NO2).
Anal. Calcd for C21H20N4O3S2: C, 57.25; H, 4.58; N, 12.72. Found:
C, 57.34; H, 4.50; N, 12.72.
1H NMR (300 MHz, DMSO-d6): δ = 2.44 (s, 3 H, SCH3), 4.95 (s, 2
H, CH2), 7.10 (d, 3J = 9.0 Hz, 2 H, Ar-H), 7.22 (br s, 2 H, NH2), 7.40
(d, 3J = 9.0 Hz, 2 H, Ar-H), 7.41 (s, 1 H, CH), 7.98 (d, 3J = 9.0 Hz,
2 H, Ar-H), 8.49 (d, 3J = 9.0 Hz, 2 H, Ar-H).
N-({4-Amino-2-(methylthio)furo[2,3-d]pyrimidin-5-yl}methyl)-
N-(2,6-diisopropylphenyl)methanesulfonamide (5j)
Yield: 60 mg (29%); white solid; mp 219.5–221 °C (n-BuOH).
IR (KBr): 3456, 3392, 3350 cm–1 (NH).
Synthesis 2012, 44, 1329–1338
© Georg Thieme Verlag Stuttgart · New York