4-Chlorothieno[3,2-d]pyrimidine → HCID 22112830, compound

HRID 564782Notes

Reaction equation

HRID 564782 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[F:27])[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[F:27])[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 219521053-Chloro-4-[(2-fluorophenyl)methoxy]aniline

Product 1

HCID 22112830HCID 22112830, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorothieno[3,2-d]pyrimidine (0.103 g, 0.60 mmol) and 3-chloro-4-(2-fluorobenzyloxy)aniline (prepared according to the published method: WO 96/09294) (0.197 g, 0.78 mmol) were reacted in 2-propanol (4.5 ml) for 4.5 hours, according to Procedure A. The product was obtained as cream prisms (0.208 g, 82%) with m.p. 231-233° C.; (Found: C, 53.39; H, 3.30; N, 9.79. C19H13ClFN3OS.HCl.H2O requires: C, 53.47; H, 3.42; N, 9.85%); δH [2H6]-DMSO 8.88 (1H, s, 2-H), 8.47 (1H, d, J 7, 6 H or 7 H) 7.88 (1H, d, J 5, 2′-H), 7.55-7.68 (3H, m), 7.33-7.49 (2H, m), 7.20-7.30 (2H, m) (6H or 7H, 5′-H, 6′-H, 3″-H, 4″-H, 5″-H, 6″-H), 5.29 (2H, s, CH2); m/z 385 (M+1+).

Sources & evidence

ORD record
ord-a03fe67174d84b84a2969fde91520b24
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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