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

HRID 60529

Reaction equation

HRID 60529 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:18])[C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([SH:19])=[N:6][C:5]=2[N:20]=1.Br[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23]>>[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]([CH3:18])[C@H:11]([CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:12][OH:13])=[N:8][C:7]([S:19][CH:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:23])=[N:6][C:5]=2[N:20]=1

Participants

3

Reactant 2

HCID 11454(1-Bromoethyl)benzeneHCID 178445912HCID 178445912, compound

Product 1

HCID 11965770(2R)-2-[{2-Amino-5-[(1-phenylethyl)thio][1,3]thiazolo[4,5-d]pyrimidin-7-yl}(methyl)amino]-4-methylpentan-1-olYield 62%

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)(methyl)amino]-4-methylpentan-1-ol (31.4 mg, 0.1 mmol) with 1-bromoethylbenzene (13.5 μL, 0.1 mmol) to give 26 mg (62% yield).

Workup

  1. customto give 26 mg (62% yield)

Sources & evidence

ORD record
ord-b40751796cd245b18d9f8f37ad7450a5
Source dataset
uspto-grants-2016_09
Patent number
US09440992B2

Linked notes

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