TFMPP hydrochloride → 3-[5-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione

HRID 2165205Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([NH:10][C:11]1[C:15]([C:16]([O:18]C)=O)=[CH:14][S:13][CH:12]=1)=[O:9].Cl.[F:21][C:22]([F:36])([F:35])[C:23]1[CH:24]=[C:25]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1>>[F:36][C:22]([F:21])([F:35])[C:23]1[CH:24]=[C:25]([N:29]2[CH2:34][CH2:33][N:32]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][N:7]3[C:16](=[O:18])[C:15]4=[CH:14][S:13][CH:12]=[C:11]4[NH:10][C:8]3=[O:9])[CH2:31][CH2:30]2)[CH:26]=[CH:27][CH:28]=1

Participants

Reactant 2

HCID 3084246TFMPP hydrochloride

HCID 15697668N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 150706883-[5-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dioneYield 96.7%

Procedure

The title compound was prepared by the procedure in Example 18 starting with 10.13 g (29 mmol) of the N-(5-bromopentyl)-N'-(4-carbomethoxythien-3-yl]urea of Example 12 and 15.47 g (58 mmol) of 1-(3-trifluoromethylphenyl)piperazine hydrochloride. There was obtained 13.08 g (96%) of the known 3-[5-[4-(3-trifluoromethylphenyl)piperazin-1-yl]pentyl]thieno[3,4-d]pyrimidine-2,4-dione (J. Press and R. Russell, U.S. Pat. No. 4,670,560) which was crystallized from CH2Cl2 /hexane to afford a white solid, mp 118°-123° C.

Sources & evidence

ORD record: ord-fc99fb4bb7cd43b883b7eae88e4e581b
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04939137

Reaction notes

Loading…