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

HRID 550752

Reaction equation

HRID 550752 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.Cl[CH:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][CH3:23]>>[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:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:22][CH3:23])=[N:6][C:5]=2[N:19]=1

Participants

3

Reactant 2

HCID 524241(1-Chloropropyl)benzeneHCID 178445911HCID 178445911, compound

Product 1

HCID 11842649(2R)-2-({2-Amino-5-[(1-phenylpropyl)thio][1,3]thiazolo[4,5-d]pyrimidin-7-yl}amino)-4-methylpentan-1-olYield 31%

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, 100 μmol) with (1-chloropropyl)benzene (15.5 μL, 100 μmol) to give 13 mg (31% yield) as an oil.

Workup

  1. customto give 13 mg (31% yield) as an oil

Sources & evidence

ORD record
ord-f3b191c93dd14989bc7303a4745678f1
Source dataset
uspto-grants-2011_05
Patent number
US07947693B2

Linked notes

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