4-Chlorothieno[3,2-d]pyrimidine → HCID 22112857, compound

HRID 564783Notes

Reaction equation

HRID 564783 reaction equation
[Cl:1][C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[NH2:16]>CC(O)C>[ClH:1].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[O:28][CH3:29])[NH:16][C:2]1[C:3]2[S:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 22112878HCID 22112878, compound

Product 1

HCID 22112857HCID 22112857, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorothieno[3,2-d]pyrimidine (0.102 g, 0.60 mmol) and 3-methoxy-4-(2-methoxybenzyloxy)aniline (prepared according to the published method: WO 96/09294) (0.181 g, 0.70 mmol) were reacted in 2-propanol (3 ml) for 75 minutes according to Procedure A. The product was obtained as off-white prisms (0.211 g, 82%) with m.p. 207-208° C.; (Found: C, 58.55; H, 4.76; N, 9.53. C21H19N3O3S.HCl requires: C, 58.55; H, 4.69; N, 9.77%); δH [2H6]-DMSO 8.85 (1H, s, 2-H), 8.41 (1H, d, J 7, 6 H or 7 H) 7.55 (1H, d, J 7, 6-H or 7-H), 7.42 (1H, d, J 9, 6′-H), 7.34 (1H, t, J 8, 4″-H), 7.29 (1H, s, 2′-H), 7.02-7.20 (3H, m, 5′-H, 3″-H, 6″-H), 6.98 (1H, t, J 8, 5″-H), 5.08 (2H, s, CH2), 3.83 and 3.79 (2x 3H, 2 x s, 2 x OCH3); m/z 393 (M+).

Sources & evidence

ORD record
ord-14b2c87ed2e7419aa4bdb9bc5c8d5634
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

Loading…