Diisopropylethylamine → tert-butyl (2S)-2-([5-(2-aminopyrimidin-5-yl)pyridin-2-yl]carbonylamino)-3,3-dimethylbutanoate

HRID 500179Notes

Reaction equation

HRID 500179 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[NH2:11][C@@H:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([C:37](O)=[O:38])=[N:35][CH:36]=2)=[CH:27][N:26]=1>CN(C)C=O>[NH2:24][C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[CH:33][C:34]([C:37]([NH:11][C@@H:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])=[O:38])=[N:35][CH:36]=2)=[CH:27][N:26]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 56776989tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochlorideHCID 672237795-(2-Aminopyrimidin-5-yl)picolinic acid

Product 1

HCID 67223273tert-butyl (2S)-2-([5-(2-aminopyrimidin-5-yl)pyridin-2-yl]carbonylamino)-3,3-dimethylbutanoateYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N-Diisopropylethylamine (1.13 mL, 6.48 mmol) was added to a mixture of tert-butyl (2S)-2-amino-3,3-dimethylbutanoate hydrochloride (0.250 g, 1.12 mmol), and 5-(2-aminopyrimidin-5-yl)pyridine-2-carboxylic acid (0.242 g, 1.12 mmol) in N,N-dimethylformamide (10 mL). The mixture was stirred at RT for 3 h, and filtered. The filtrate was diluted with methanol (10 mL). The resulting solution was purified by RP-HPLC (pH 10) to give the desired product (182 mg, 42.3%). LCMS: (M+H)=386.2.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with methanol (10 mL)
  3. customThe resulting solution was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record
ord-55319152177a46878b5dc1ff750dc8c2
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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