Acetic Acid → 1,1-Dimethylethyl 4-[5-[(1-methylethyl)amino]-4-pyrimidinyl]-1-piperazinecarboxylate

HRID 2395749Notes

Reaction equation

HRID 2395749 reaction equation
C([BH3-])#N.[Na+].[CH3:5][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[N:22]=[CH:21][N:20]=[CH:19][C:18]=2[NH2:23])[CH2:13][CH2:12]1)=[O:10])[CH3:7].[CH3:25][C:26]([CH3:28])=O.C(O)(=O)C>CO.[OH-].[Na+].ClCCl>[CH3:7][C:6]([CH3:24])([O:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[N:22]=[CH:21][N:20]=[CH:19][C:18]=2[NH:23][CH:26]([CH3:28])[CH3:25])[CH2:15][CH2:16]1)=[O:10])[CH3:5]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 21477601HCID 21477601, compound

Product 1

HCID 214776211,1-Dimethylethyl 4-[5-[(1-methylethyl)amino]-4-pyrimidinyl]-1-piperazinecarboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of sodium cyanoborohydride (0.13 g) in methanol (4 ml) is added to a mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[5-amino-6-pyrimidinyl]piperazine (PREPARATION 28, 0.44 g), acetone (3 ml), and glacial acetic acid (0.4 ml) in methanol (7 ml) at 0°. The mixture is stirred at 20°-25° for 72 h. The reaction is diluted with an aqueous sodium hydroxide solution (10%) and dichloromethane. The phases are separated and the organic phase is washed with water and the concentrated to a colorless liquid which is flash chromatographed on silica gel eluting with methanol/chloroform (1/99). The appropriate fractions are pooled and concentrated to give the title compound, NMR (CDCl3) 1.26, 1.49, 3.2, 3.44, 3.5-3.62, 7.89 and 8.33 δ.

Workup

  1. customThe phases are separated
  2. washthe organic phase is washed with water
  3. concentrationthe concentrated to a colorless liquid which
  4. customchromatographed on silica gel eluting with methanol/chloroform (1/99)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5dd3477bfdc243668ddd08d353ca4a6c
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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