Triphosgene → 7-(4-chlorophenyl)-5-(methylthio)-8-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one

HRID 271419Notes

Reaction equation

Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[C:24]([NH:32][NH2:33])[N:23]=[C:22]([S:34][CH3:35])[N:21]=2)=[CH:16][CH:15]=1>C1COCC1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[N:21]=[C:22]([S:34][CH3:35])[N:23]3[C:2](=[O:4])[NH:33][N:32]=[C:24]3[C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of triphosgene (2.08 g, 7.04 mmol) in THF (10 mL) at room temperature under argon was added a suspension of 4-(4-chlorophenyl)-6-hydrazinyl-2-(methylthio)-5-phenylpyrimidine (3.52 mmol) in THF (5 mL). The reaction mixture was stirred overnight. Analysis by HPLC/MS indicated that no starting material remained. The reaction mixture was cooled to 0° C. in an ice bath and ice water (50 mL) was added. After stirring for 30 min, the solid precipitate was collected and further washed with water (50 mL). After drying, the title compound (1.25 g) was obtained as an off-white solid. HPLC/MS: retention time=3.51 min, [M+H]30 =369.

Workup

stirringAfter stirring for 30 min
customthe solid precipitate was collected
washfurther washed with water (50 mL)
customAfter drying

Sources & evidence

ORD record: ord-1a3e743fee7a46c28158701d5db8a54e
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452892B2

Reaction notes

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