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

HRID 2165199Notes

Reaction equation

HRID 2165199 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH:9][C:10]1[C:14]([C:15]([O:17]C)=O)=[CH:13][S:12][CH:11]=1)=[O:8].Cl.[F:20][C:21]([F:35])([F:34])[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1>>[F:35][C:21]([F:20])([F:34])[C:22]1[CH:23]=[C:24]([N:28]2[CH2:33][CH2:32][N:31]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:15](=[O:17])[C:14]4=[CH:13][S:12][CH:11]=[C:10]4[NH:9][C:7]3=[O:8])[CH2:30][CH2:29]2)[CH:25]=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 3084246TFMPP hydrochlorideHCID 15697666N-(4-bromobutyl)-N'-(4-carbomethoxythien-3-yl)urea

Product 1

HCID 150706923-[4-[4-(3-Trifluoromethylphenyl)piperazin-1-yl]butyl]thieno[3,4-d]pyrimidine-2,4-dioneYield 34.2%

Procedure

The above urea (12.41 g, 37.5 mmol) was reacted with 1-(3-trifluoromethylphenyl)piperazine hydrochloride (15 g, 56.2 mmol) as described in Example 12 to produce 5.8 g (34%) of the known 3-[4-[4-(3-trifluoromethylphenyl)piperazin-1-yl]butyl]thieno[3,4-d]pyrimidine-2,4-dione (J. Press and R. Russell, U.S. Pat. No. 4,670,560) after recrystallization from CH2Cl2 /hexane as a white solid, mp 126°-128° C.

Sources & evidence

ORD record
ord-3850487022124ad09b6bb9fd8c1344c9
Source dataset
uspto-grants-1990_07
Patent number
US04939137

Reaction notes

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