N-(tert-butoxycarbonyl)glycine → Tert-butoxycarbonylamino-acetic acid 4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester

HRID 28577Notes

Reaction equation

HRID 28577 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[N:3]=1.[C:27]([O:31][C:32]([NH:34][CH2:35][C:36](O)=[O:37])=[O:33])([CH3:30])([CH3:29])[CH3:28]>ClCCl>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:36](=[O:37])[CH2:35][NH:34][C:32]([O:31][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:33])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH2:25][CH3:26])[N:3]=1

Participants

4

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 10406874Benzenemethanol, 4-((2-amino-6-(5-chloro-2-ethoxyphenyl)-4-pyrimidinyl)amino)-

Product 1

HCID 68983979Tert-butoxycarbonylamino-acetic acid 4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of the title compound of Example 44 (0.400 g, 1.08 mmol), N-(tert-butoxycarbonyl)-glycine (0.227 g, 1.29 mmol) and 4-dimethyl-amino-pyridine (0.184 g, 1.51 mmol) in dichloromethane (20 ml) was added 1-[3-(dimethyl-amine)-propyl]-3-ethyl carboduimide (0.282 g, 1.51 mmol). After stirring for 6 hours, the mixture was purified by flash chromatography on silica gel eluting in ethyl acetate-hexane (2:3) to provide tert-butoxycarbonylamino-acetic acid 4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-benzyl ester.

Workup

  1. customthe mixture was purified by flash chromatography on silica gel eluting in ethyl acetate-hexane (2:3)

Sources & evidence

ORD record
ord-306c6a4a5b184c1fb9fcfab6784119dc
Source dataset
uspto-grants-2008_09
Patent number
US07419984B2

Reaction notes

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