1-(1-Bromoethyl)-3-(trifluoromethyl)benzene → (2R)-2-{[2-Amino-5-({1-[3-(trifluoromethyl)phenyl]ethyl}thio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino}-4-methylpentan-1-ol

HRID 60526Notes

Reaction equation

HRID 60526 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:18])=[N:6][C:5]=2[N:19]=1.Br[CH:21]([C:23]1[CH:24]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:27][CH:28]=1)[CH3:22]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([NH:10][C@H:11]([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:12][OH:13])=[N:8][C:7]([S:18][CH:21]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:30])([F:31])[F:32])[CH:24]=3)[CH3:22])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 27756241-(1-Bromoethyl)-3-(trifluoromethyl)benzeneHCID 178445911HCID 178445911, compound

Product 1

HCID 11964574(2R)-2-{[2-Amino-5-({1-[3-(trifluoromethyl)phenyl]ethyl}thio)[1,3]thiazolo[4,5-d]pyrimidin-7-yl]amino}-4-methylpentan-1-olYield 81%

Procedure

The title compound was synthesized as a mixture of two diastereomers by general method A from the reaction of (2R)-2-[(2-amino-5-mercapto[1,3]thiazolo[4,5-d]pyrimidin-7-yl)amino]-4-methylpentan-1-ol (30 mg, 0.1 mmol) with 3-(1-bromoethyl)trifluoromethylbenzene (15.5 μL, 0.1 mmol) to give 38 mg (81% yield) as an oil.

Workup

  1. customto give 38 mg (81% yield) as an oil

Sources & evidence

ORD record
ord-105bf5c0b4654fc9b8b115a3cc273af8
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Reaction notes

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