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

HRID 60535Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

DIPEA (0.83 mL, 4.75 mmol) was added to a solution of 7-chloro-5-{[(1S)-1-phenylethyl]thio}[1,3]thiazolo[4,5-d]pyrimidin-2-amine (0.49 g, 1.52 mmol) and (2R)-2-amino-4-fluoro-4-methylpentan-1-ol (2 mmol) in NMP (2 mL) and the reaction mixture was stirred at 120° C. for 22 h. HPLC purification provided the title compound (0.22 g, 17% yield).

Workup

customHPLC purification

Sources & evidence

ORD record: ord-a13a3914614649ffbe4c91f745981c9a
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440992B2

Reaction notes

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