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ISTANBULLU ET AL.
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compounds were crystallized from ethanol, methanol, ethyl acetate,
or tetrahydrofuran.
J = 8.0 Hz), 8.01 (d, 2H, J = 8.0 Hz), 8.60 (s, 1H), and 10.69 (br, 1H).
13C‐NMR (CDCl3, 100 MHz) δ: 127.8 (2C), 129.4 (2C), 130.9, 134.0,
139.3, 149.2, 154.8, 159.5, 165.5, and 165.9. MS (ESI+): m/z: 290.9
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)acetamide (L1)[28]
Yield 71% (yellow solid). mp. 205°C. FTIR νmax cm−1: 1,724 and 1,584.
1H‐NMR (dimethyl sulfoxide DMSO‐d6, 400 MHz) δ: 2.21 (s, 3H), 9.05
(s, 1H), and 12.78 (br, 1H). 13C‐NMR (DMSO‐d6, 100 MHz) δ: 23.1,
140.4, 149.7, 153.4, 158.9, 166.0, and 170.7. MS (ESI+): m/z: 229.1 [M
+H]+ and 231.1 [M+2+H]+. Anal. (C7H5ClN4OS.0.5H2O.0.33CH3OH)
calcd: C 35.47, H 2.97, N 22.57, S 12.92; found: C 35.85, H 3.36, N
22.55, S 12.59.
[M+H]+ and 292.9 [M+2+H]+, Anal. (C12H7ClN4OS.0.5H2O.0.1C6H14
)
calcd: C 49.08, H 3.07, N 18.17, S 10.40; found: 48.93, H 2.97,
N 17.94, S 10.33.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)‐2‐methyl benzamide (L7)
Yield 77% (yellow solid). mp. 172°C. FTIR νmax cm–1: 1,676 and 1,575.
1H‐NMR (DMSO‐d6, 400 MHz) δ: 2.41 (s, 3H), 7.32–7.36 (m, 2H), 7.48
(d, 1H, J = 7.6 Hz), 7.64 (d, 1H, J = 7.6 Hz), 9.13 (s, 1H), and 13.21 (br,
1H). 13C‐NMR (DMSO‐d6, 100 MHz) δ: 20.1, 126.2, 128.9, 131.5,
131.9, 133.2, 137.3, 140.3, 150.1, 153.5, 159.2, 165.9, and 169.3. MS
(ESI+): m/z: 305.0 [M+H]+ and 307.0 [M+2+H]+. Anal. (C13H9ClN4
OS.0.2C2H5OH) calcd: C 51.26, H 3.27, N 17.84, S 10.21; found:
50.95, H 3.51, N 17.49, S 10.35.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)propionamide (L2)
Yield 73% (yellow solid). mp. 241°C. FTIR νmax cm−1: 1,692 and 1,572.
1H‐NMR (DMSO‐d6, 400 MHz) δ: 1.10 (t, 3H, t, J = 7.6 Hz), 2.54
(q, 2H, J = 7.6 Hz), 9.07 (s, 1H), and 12.75 (br, 1H). 13C‐NMR (DMSO‐
d6, 100 MHz) δ: 9.1, 28.9, 140.3, 149.7, 153.2, 158.8, 165.9, and
174.4. MS (ESI+): m/z: 243.2 [M+H]+ and 245.2 [M+2+H]+, Anal.
(C8H7ClN4OS) calcd: C 39.59, H 2.91, N 23.09, S 13.21; found: C
39.77, H 3.10, N 23.47, S 13.45.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)‐2‐methoxybenzamide (L8)
Yield 52% (yellow solid). mp. 220°C (decomposition). FTIR νmax
cm–1: 1,673 and 1,575. 1H‐NMR (DMSO‐d6, 400 MHz) δ: 3.90
(s, 3H), 7.02–7.22 (m, 2H), 7.56–7.73 (m, 2H), 9.11 (s, 1H), and
11.33 (br, 1H). 13C‐NMR: n.d. MS (ESI+): m/z: 321.0 [M+H]+ and
323.1 [M+2+H]+. Anal. (C13H9ClN4O2S.0.1H2O.0.2C4H8O2) calcd:
C 48.73, H 3.20, N 16.47, S 9.42; found: C 48.63, H 3.51, N 16.12,
S 9.13.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin ‐2‐yl)butyramide (L3)
Yield 72% (beige solid). mp. 194°C. FTIR νmax cm−1: 1,709 and 1,585.
1H‐NMR (DMSO‐d6, 400 MHz) δ: 0.91 (t, 3H, J = 7.6 Hz), 1.63 (m, 2H,
J = 7.2 Hz), 2.48 (br, 2H), 9.04 (s, 1H), and 12.77 (br, 1H). 13C‐NMR
(DMSO‐d6, 100 MHz) δ: 13.9, 18.2, 37.4, 140.3, 149.8, 153.2, 158.8,
165.8, and 173.6. MS (ESI+): m/z: 257.0 [M+H]+ and 259.1 [M+2+H]+.
2‐Chloro‐N‐(5‐chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)benzamide (L9)
Yield 77% (yellow solid). mp. 188°C (decomposition). FTIR νmax cm–1
:
Anal. (C9H9ClN4OS.0.2H2O.0.2CH3OH) calcd:
C
41.43,
H
3.85,
N 21.01, S 12.02; found: C 41.33, H 3.43, N 20.83, S 11.92.
1,678 and 1,579. 1H‐NMR (CDCl3, 400 MHz) δ: 7.45–7.50 (m, 2H),
7.53–7.57 (m, 1H), 7.95 (dd, 1H, J1 = 2.0 Hz, J2 = 7.4 Hz), 8.65 (s, 1H),
and 10.56 (br, 1H). 13C‐NMR (CDCl3, 100 MHz) δ: 127.8, 131.0,
131.4, 131.4, 133.8, 139.2, 145.7, 149.2, 154.8, 158.8, 164.5, and
165.8. MS (ESI+): m/z: 325.00 [M+H]+, 327.0 [M+2+H]+, and 329.0
[M+4+H]+. Anal. (C12H6Cl2N4OS.0.5C4H8O2) calcd: C 45.54, H 2.73,
N 15.17, S 8.68; found: C 45.73, H 2.37, N 15.52, S 9.01.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)isobutyramide (L4)
Yield 45% (light green solid). mp. 179°C. FTIR νmax cm−1: 1,686 and
1,583. 1H‐NMR (DMSO‐d6, 400 MHz) δ: 1.14 (d, 6H, J = 6.8 Hz), 2.81
(m, 1H, J = 6.8 Hz), 9.05 (s, 1 H), and 12.80 (br, 1H). 13C‐NMR (DMSO‐
d6, 100 MHz) δ: 19.2, 34.6, 140.3, 149.7, 153.2, 159.0, 165.9, and
177.5. MS (ESI+): m/z: 257.0 [M+H]+ and 259.2 [M+2+H]+. Anal.
(C9H9ClN4OS.0.33H2O.0.25CH3OH) calcd: C 41.05, H 3.97, N 20.70,
S 11.84; found: C 41.10, H 3.95, N 20.83, S 11.42.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)‐2‐fluorobenzamide (L10)
Yield 47% (yellow solid). mp. 218°C. FTIR νmax cm–1: 1,667 and 1,576.
1H‐NMR (DMSO‐d6, 400 MHz) δ: 7.36–7.42 (m, 2H), 7.65–7.71
(m, 1H), 7.80 (d, 1H, J = 7.2 Hz), 9.13 (s, 1H), and 10.35 (br, 1H). 13C‐
NMR (DMSO‐d6, 100 MHz) δ: 117.1, 121.7, 125.2, 130.9, 135.0,
140.3, 150.3, 153.6, 158.9, 161.2, 164.8, and 165.8. MS (ESI+): m/z:
309.1 [M+H]+ and 311.1 [M+2+H]+. Anal. (C12H6ClFN4OS.0.33H2-
O.0.33CH3OH) calcd: C 45.54, H 2.47, N 17.23, S 9.81; found:
C 45.85, H 2.09, N 17.68, S 9.86.
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)cyclohexane
carboxamide (L5)
Yield 62% (gray solid). mp. 192°C. FTIR νmax cm–1: 1,694 and 1,579.
1H‐NMR (DMSO‐d6, 400 MHz) δ: 1.16–1.87 (m, 10H), 2.56 (tt, 1H,
J1 = 3.6 Hz, J2 = 11.2 Hz), 9.05 (s, 1H), and 12.72 (br, 1H). 13C‐NMR
(DMSO‐d6, 100 MHz) δ: 25.4 (2C), 25.6, 29.0 (2C), 44.0, 140.3, 149.8,
153.2, 159.0, 165.9, and 176.5. MS (ESI+): m/z: 297.0 [M+H]+ and
299.1 [M+2+H]+. Anal. (C12H13ClN4OS.0.5H2O.0.33CH3OH) calcd: C
46.66, H 5.01, N 17.41, S 9.96; found: C 46.43, H 4.63, N 17.22,
S 9.90.
2‐Bromo‐N‐(5‐chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)benzamide (L11)
Yield 65% (dark beige solid). mp. 216 °C. FTIR νmax cm–1: 1,698 and
1,581. 1H‐NMR (DMSO‐d6, 400 MHz) δ: 7.47–7.56 (m, 2H), 7.69 (dd,
1H, J1 = 2.0 Hz, J2 = 7.2 Hz), 7.77 (dd, 1H, J1 = 1.2 Hz, J2 = 7.4 Hz), 9.11
(s, 1H), and 13.46 (br, 1H). 13C‐NMR (DMSO‐d6, 100 MHz) δ: 119.6,
128.3, 130.0, 133.0, 133.5, 136.0, 140.3, 150.4, 153.6, 158.7, 165.8,
and 167.7. MS (ESI+): m/z: 368.8 [M+H]+, 370.9 [M+2+H]+, and 372.9
N‐(5‐Chlorothiazolo[5,4‐d]pyrimidin‐2‐yl)benzamide (L6)
Yield 75% (yellow solid). mp. 229°C. FTIR νmax cm–1: 1,671 and 1,577.
1H‐NMR (CDCl3, 400 MHz) δ: 7.55 (t, 2H, J = 8.0 Hz), 7.68 (t, 1H,