5-Amino-4,6-dichloropyrimidine → tert-Butyl 4-(5-amino-6-chloropyrimidin-4-yl)piperazine-1-carboxylate

HRID 1192298Notes

Reaction equation

HRID 1192298 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=1.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>C1(C)C=CC=CC=1>[C:13]([O:12][C:10]([N:17]1[CH2:22][CH2:21][N:20]([C:2]2[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[CH:4][N:3]=2)[CH2:19][CH2:18]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 794345-Amino-4,6-dichloropyrimidineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 71748362tert-Butyl 4-(5-amino-6-chloropyrimidin-4-yl)piperazine-1-carboxylateYield 99.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 4,6-dichloro-5-aminopyrimidine (1 g, 6.1 mmol) in TEA (2 mL) and toluene (10 mL) was added 1-Boc-piperazine (2.3 g, 12.3 mmol). The mixture was refluxed for 12 hours. The solvent was removed and the residue was subject to chromatography on silica gel to afford the product 4-(5-amino-6-chloropyrimidin-4-yl)-piperazin-1-carboxylic acid tert-butyl ester (1.9 g, 99%). 1H NMR (CDCl3, 400 Hz) δ 8.16 (s, 1H), 3.87 (s, 2H), 3.56 (m, 4H), 3.29 (m, 4H), 1.49 (s, 9H). MS (ESI+) [M+H]+ 314.

Workup

  1. temperatureThe mixture was refluxed for 12 hours
  2. customThe solvent was removed

Sources & evidence

ORD record
ord-85cf74fa945940f08f2d39f2f9d0f5ae
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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