4-Chloro-5-methylthieno[2,3-d]pyrimidine → HCID 22112897, compound

HRID 564791Notes

Reaction equation

HRID 564791 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Cl: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[F:28])[NH2:16]>CC(O)C>[ClH:1].[Cl: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[F:28])[NH:16][C:2]1[C:3]2[C:10]([CH3:11])=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 2902254-Chloro-5-methylthieno[2,3-d]pyrimidineHCID 219521053-Chloro-4-[(2-fluorophenyl)methoxy]aniline

Product 1

HCID 22112897HCID 22112897, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-5-methylthieno[2,3-d]pyrimidine (commercially available from Maybridge Chemical Co. Ltd.) (0.092 g, 0.50 mmol) and 3-chloro-4-(2-fluorobenzyloxy)aniline (prepared according to the published method: WO 96/09294) (0.164 g, 0.65 mmol) were reacted in 2-propanol (3.5 ml) for 4 hours, according to Procedure A. The product was obtained as cream plates (0.156 g, 72%) with m.p. 193-196° C.; (Found: C, 55.17; H, 3.77; N, 9.56. C20H15ClFN3OS.HCl requires: C, 55.05; H, 3.70; N, 9.63%); δH [2H6]-DMSO 8.39 (1H, s, 2-H), 8.37 (1H, br s, N—H), 7.75 (1H, d, J 4, 2′-H), 7.49-7.59 (2H, m), 7.34-7.44 (1H, m), 7.15-7.32 (4H, m) (6-H, 5′-H, 6′-H, 3″-H, 4″-H, 5″-H, 6″-H), 5.19 (2H, s, CH2), 2.69 (3H, s, 5-CH3); m/z 400 (M+1+).

Workup

  1. customThe product was obtained as cream plates (0.156 g, 72%) with m.p. 193-196° C.

Sources & evidence

ORD record
ord-1920d7f2fe93498fbb7ea6b7aec5675b
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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