4-Chlorothieno[3,2-d]pyrimidine → HCID 22112870, compound

HRID 564789Notes

Reaction equation

HRID 564789 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.[CH:11]1([CH2:17][O:18][C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CC(O)C>[ClH:1].[CH:11]1([CH2:17][O:18][C:19]2[CH:25]=[CH:24][C:22]([NH:23][C:2]3[C:3]4[S:10][CH:9]=[CH:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[CH:21][CH:20]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 27358214-Chlorothieno[3,2-d]pyrimidineHCID 156816514-(Cyclohexylmethoxy)aniline

Product 1

HCID 22112870HCID 22112870, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chlorothieno[3,2-d]pyrimidine (0.171 g, 1.00 mmol) and 4-cyclohexylmethoxy-aniline (prepared according to the published method: WO 96/09294) (0.205 g, 1.00 mmol) were reacted in 2-propanol (5 ml) for 5 hours, according to Procedure A. The product was obtained as cream prisms (0.255 g, 68%) with m.p. 232-233° C.; (Found: C, 60.65; H, 5.68; N, 11.25. C19H21N3OS.HCl requires: C, 60.71; H, 5.90; N, 11.23%); δH [2H6]-DMSO 11.11 (1H, br s, NH), 8.71 (1H, s, 2-H), 8.41 (1H, d, J 7,6 H or 7 H) 7.44-7.58 (3H, m, 6H or 7H, 2′-H, 6′-H), 7.03 (2H, d, J 9, 3′-H, 5′-H), 3.84 (2H, s, CH2), 1.58-1.90 (6H, m) and 0.98-1.33 (5H, m) (cyclohexyl-H11); m/z 339 (M+).

Sources & evidence

ORD record
ord-1292bf54059e4a298f5a7b74815bba34
Source dataset
uspto-grants-2001_01
Patent number
US06169091A

Reaction notes

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