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

HRID 1768175Notes

Reaction equation

HRID 1768175 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-b608c427fd3648a198ece541ae3dcf2d
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

Loading…