Acetonitrile → HCID 86739371, compound
Reaction equation
[Cl:1][CH2:2][C:3]1[N:4]=[C:5]2[S:12][CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:6]2[C:7](=[O:9])[CH:8]=1.[C:19]1([P:25]([C:32]2C=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[C:38](#N)C>>[Cl-:1].[C:13]1([C:10]2[N:6]3[C:7](=[O:9])[CH:8]=[C:3]([C:2]4[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=4[P+:25]([CH3:38])([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:4]=[C:5]3[S:12][CH:11]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Procedure
7-chloromethyl-3-phenyl-5H-thiazolo[3,2-a]pyrimidine-5-one, m.p. 194°-195° C. (7.8 g), prepared according to Example 5, was reacted with triphenylphosphine (8 g) in acetonitrile (250 ml) under stirring at the reflux temperature for 24 hours. After cooling the solution was concentrated in vacuo to a small volume, diluted with isopropyl ether and the precipitate was filtered to give 11 g of [3-phenyl-5H-thiazolo[3,2-a]pyrimidine-5-one-7-yl]-methyl-triphenylphosphonium chloride, which was suspended in dimethylsulfoxide (50 ml) and treated with potassium tert-butoxide (2.46 g) dissolved in dimethylsulfoxide (50 ml) under stirring at room temperature. The solution of the ylide so obtained was reacted with 3-pyridine-carboxaldehyde (2.36 g) at room temperature for 60 minutes then the reaction mixture was diluted with ice water and neutralized with NaH2PO4.
Workup
- temperatureAfter cooling the solution
- concentrationwas concentrated in vacuo to a small volume
- additiondiluted with isopropyl ether
- filtrationthe precipitate was filtered
Sources & evidence
- ORD record
- ord-047f37418241474ba2189f4357e7095c
- Source dataset
- uspto-grants-1984_04
- Patent number
- US04444773
Reaction notes
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