Water → 7-Chloro-5-{[(1S)-1-(2-fluorophenyl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine

HRID 550767Notes

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][C:25]=3[F:30])[CH3:23])=[N:16][C:15]=2[N:31]=1.O>O1CCOCC1>[Cl:3][C:19]1[C:14]2[S:13][C:12]([NH2:11])=[N:31][C:15]=2[N:16]=[C:17]([S:21][C@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[F:30])[CH3:23])[N:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

POCl3 (2.77 mL, 29.7 mmol) was added to DMF (3.07 mL, 39.6 mmol) in dioxane (30 mL). After 30 minutes this mixture was added to a solution of 2-amino-5-{[(1S)-1-(2-fluorophenyl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-ol (6.38 g, 19.8 mmol) in dioxane (100 mL). After 30 minutes POCl3 (2.77 mL, 29.7 mmol) was added, the reaction mixture was heated to 80° C. for 2 h. After cooling to room temperature, water (20 mL) was carefully added and the resulting mixture was stirred at 80° C. for 30 minutes and at room temperature for 2 h. The reaction mixture was poured into water and the formed precipitate was collected. The solid was purified by flash column chromatography (5% MeOH in CHCl3) to give the title compound (5.91 g, 88% yield).

Workup

temperatureAfter cooling to room temperature
customthe formed precipitate was collected
customThe solid was purified by flash column chromatography (5% MeOH in CHCl3)

Sources & evidence

ORD record: ord-c88211377c3047d9943a2aed9ba911dc
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947693B2

Reaction notes

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