Dimethylformamide → (S)-7-chloro-5-((1-phenylethyl)thio)thiazolo[4,5-d]pyrimidin-2-amine

HRID 550762Notes

Reaction equation

O=P(Cl)(Cl)[Cl:3].CN(C=O)C.[NH2:11][C:12]1[S:13][C:14]2[C:19](O)=[N:18][C:17]([S:21][C@H:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])=[N:16][C:15]=2[N:30]=1>O1CCOCC1>[Cl:3][C:19]1[C:14]2[S:13][C:12]([NH2:11])=[N:30][C:15]=2[N:16]=[C:17]([S:21][C@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:23])[N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

POCl3 (1 mL) was added to DMF (1 mL) in dioxane (6 mL). 2-Amino-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-ol (1 g, 3.3 mmol) was added to the reaction in one portion. POCl3 (1 mL) was added and the reaction mixture was heated to 80° C. for about 30 min. The reaction was cooled to room temperature and poured onto ice. The resulting mixture was heated at reflux for about 5 h. The mixture was allowed to attain room temperature and was then extracted with EtOAc. The organic layer was passed through a layer of silica gel and concentrated to dryness to give the title compound (1 g, 95% yield).

Workup

temperatureThe reaction was cooled to room temperature
additionpoured onto ice
temperatureThe resulting mixture was heated
temperatureat reflux for about 5 h
customto attain room temperature
extractionwas then extracted with EtOAc
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-816fba36c88342c6a2966e13f3c9bad2
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947693B2

Reaction notes

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