Potassium Carbonate → 4-(4-Hydroxyphenyl)-1-(3,4-dihydro-3-methyl-2-phenylpyrimidin-4-on-6-ylmethyl)piperazine
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:15][C:16]1[N:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]([CH3:28])[C:18](=[O:29])[CH:17]=1.C([O-])([O-])=O.[K+].[K+]>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:15][C:16]3[N:21]=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:19]([CH3:28])[C:18](=[O:29])[CH:17]=3)[CH2:10][CH2:9]2)=[CH:6][CH:7]=1Participants
4
Procedure
According to the same procedure as described in Example 20, starting from 3.39 g (19 mmol) of 1-(4-hydroxyphenyl)piperazine and 4.20 g (17.9 mmol) of 6-chloromethyl-3,4dihydro-3-methyl-2-phenylpyrimidin-4-one, using 1.24 g (9 mmol) of K2CO3, 4.42 g (=65.6% yield) of 4-(4-hydroxyphenyl)-1-(3,4-dihydro-3-methyl-2-phenylpyrimidin-4-on-6-ylmethyl)piperazine were obtained; melting point 206°-207° C., analysis: C22H24N4O2 (MW 376.46) calc. C 70.19 H6.43 , N 14.88; found C 69.2, H 6.4, N 14.5%. For workup of the reaction mixture, the DMF had been evaporated off in vacuo, the residue had been taken up in water/CH2Cl2 and neutralized, and the CH2Cl2 extract residue had been crystallized from CH3OH.
Sources & evidence
- ORD record
- ord-3c61cb17e4514386bfdf5b93fbbdd036
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859670
Reaction notes
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