4-Chlorothieno[3,2-d]pyrimidine → HCID 22112850, compound

HRID 564781Notes

Reaction equation

HRID 564781 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.[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28])[NH2:15]>CC(O)C>[ClH:1].[Cl:11][C:12]1[CH:13]=[C:14]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][CH3:28])[NH:15][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 19626987HCID 19626987, compound

Product 1

HCID 22112850HCID 22112850, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorothieno[3,2-d]pyrimidine (0.102 g, 0.60 mmol) and 3-chloro-4-(2-methoxybenzyloxy)aniline (prepared according to the published method: WO 96/09294) (0.161 g, 0.65 mmol) were reacted in 2-propanol (4 ml) for 1.25 hours, according to Procedure A. The product was obtained as pale cream prisms (0.203 g, 78%) with m.p. 210-212° C.; (Found: C, 55.28; H, 4.00; N, 9.44. C20H16ClN3O2S.HCl requires: C, 55.31; H, 3.92; N, 9.67%); δH [2H6]-DMSO 11.19 (1H, br s, NH), 8.88 (1H, s, 2-H), 8.48 (1H, d, J 7, 6 H or 7 H) 7.87 (1H, d, J 5, 2′-H), 7.55-7.62 (2H, m, 6′-H, 4″-H), 7.48 (1H, d, J 7, 6H or 7H), 7.28-7.40 (2H, m, 5′-H, 6″-H), 7.09 (1H, d, J 9, 3″-H), 7.00 (1H, t, J 9, 5″-H), 5.22 (2H, s, CH2), 3.85 (3H, s, OCH3).

Sources & evidence

ORD record
ord-12ffbe29f41741e9b49370dbe20c51dc
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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