Triethylamine → tert-Butyl 4-(6-chloro-2-methylpyrimidin-4-yl)piperazine-1-carboxylate

HRID 2289545Notes

Reaction equation

HRID 2289545 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([Cl:8])[CH:3]=1.[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[CH2:22](N(CC)CC)C>C(O)C>[CH3:22][C:6]1[N:5]=[C:4]([Cl:8])[CH:3]=[C:2]([N:19]2[CH2:20][CH2:21][N:16]([C:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:15])[CH2:17][CH2:18]2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709434,6-DichloropyrimidineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 18697994tert-Butyl 4-(6-chloro-2-methylpyrimidin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dichloropyrimidine (24.79 g) and 1-(tert-butoxycarbonyl)piperazine (27.41 g) were stirred in ethanol (500 ml) and triethylamine (41 ml) overnight. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The organic phase was dried (Na2SO2), and evaporated to give 2-methyl-4-chloro-6-[1-(tert-butoxycarbonyl]piperazin-4-yl)pyrimidine as a solid (41.5 g); NMR (CDCl3): 6.35 (s, 1H), 3.65 (m, 4H), 3.5 (m, 4H), 2.5 (s, 3H), 1.45 (s, 9H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. dry with materialThe organic phase was dried (Na2SO2)
  5. customevaporated

Sources & evidence

ORD record
ord-75a61ae151de4d89af99206991ab1e46
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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