Water → (2R)-2-[(2-Amino-5-{[(1S)-1-(2-fluorophenyl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-fluoro-4-methylpentan-1-ol

HRID 60539Notes

Reaction equation

CCN(C(C)C)C(C)C.Cl[C:11]1[C:12]2[S:29][C:28]([NH2:30])=[N:27][C:13]=2[N:14]=[C:15]([S:17][C@H:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])[CH3:19])[N:16]=1.[NH2:31][C@H:32]([CH2:35][C:36]([F:39])([CH3:38])[CH3:37])[CH2:33][OH:34].O>CN1C(=O)CCC1>[NH2:30][C:28]1[S:29][C:12]2[C:11]([NH:31][C@H:32]([CH2:35][C:36]([F:39])([CH3:38])[CH3:37])[CH2:33][OH:34])=[N:16][C:15]([S:17][C@H:18]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[F:26])[CH3:19])=[N:14][C:13]=2[N:27]=1

Participants

Conditions

Temperature: 120 °C

Procedure

DIPEA (2.09 mL, 12.0 mmol) was added to 7-chloro-5-{[(1S)-1-(2-fluorophenyl)ethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine (1.36 g, 4.0 mmol) and (2R)-2-amino-4-fluoro-4-methylpentan-1-ol (4 mmol) in NMP (3 mL). After stirring the reaction mixture at 120° C. for 22 h it was poured into water and the precipitate was collected by filtration. The solid was purified by flash column chromatography (a stepwise gradient of 5%-10% MeOH in CHCl3) and preparative HPLC to give the title compound (0.22 g, 13% yield).

Workup

filtrationthe precipitate was collected by filtration
customThe solid was purified by flash column chromatography (a stepwise gradient of 5%-10% MeOH in CHCl3) and preparative HPLC

Sources & evidence

ORD record: ord-1be72a76545b41aa83ce6c5605da7aec
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440992B2

Reaction notes

Loading…