[4-(6-Azido-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester → [4-(6-Amino-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1993592Notes

Reaction equation

HRID 1993592 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]2[CH:20]=[C:19]([N:21]=[N+]=[N-])[N:18]=[CH:17][N:16]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][C:15]2[CH:20]=[C:19]([NH2:21])[N:18]=[CH:17][N:16]=2)=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 58659413[4-(6-Azido-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58659458[4-(6-Amino-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of [4-(6-azido-pyrimidin-4-ylmethyl)-phenyl]-carbamic acid tert-butyl ester (870 mg, 2.66 mmol) and 10% Pd/C (174 mg) in MeOH (35 mL) is stirred for 1.5 h at rt and a hydrogen atmosphere. The reaction mixture is filtered through a plug of celite (washing the filter cake with copious amounts of MeOH). The filtrate is concentrated in vacuo to afford the title compound as a beige solid: ES-MS: 301.1 [M+H]+; single peak at tR=6.25 min (System 2).

Workup

  1. filtrationThe reaction mixture is filtered through a plug of celite (
  2. washwashing the filter cake with copious amounts of MeOH)
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-fa32096b3cc44c61942405e7bccfd940
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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