4,5-Diaminopyrimidine → 4-Amino-5-[(1-t-butoxycarbonylpiperidin-4-yl)amino)pyrimidine

HRID 1365948

Reaction equation

HRID 1365948 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[NH2:1][C:2]1[C:7]([NH:8][CH:19]2[CH2:20][CH2:21][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])[CH2:17][CH2:18]2)=[CH:6][N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 837034,5-DiaminopyrimidineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 222932024-Amino-5-[(1-t-butoxycarbonylpiperidin-4-yl)amino)pyrimidine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 4,5-diaminopyrimidine (1.0 g, 9.1 mmol), N-(t-butoxycarbonyl)-4-piperidone (3.0 g, 15 mmol) and sodium triacetoxyborohydride (1.2 g, 5.6 mmol) in dichloroethane (60 mL) was stirred at room temperature for 3 d. The reaction was partitioned between chloroform (200 mL) and 3N sodium hydroxide (30 mL). After drying over magnesium sulfate, the organic phase was concentrated to give the title compound as a tan gum. MS 294 (M+1)

Workup

  1. customThe reaction was partitioned between chloroform (200 mL) and 3N sodium hydroxide (30 mL)
  2. dry with materialAfter drying over magnesium sulfate
  3. concentrationthe organic phase was concentrated

Sources & evidence

ORD record
ord-71bc0164f2604ca891737089afd30eaf
Source dataset
uspto-grants-2011_02
Patent number
US07893052B2

Linked notes

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