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

HRID 2053069Notes

Reaction equation

HRID 2053069 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.C(N(CC)CC)C.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>ClCCl>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 58878061tert-Butyl 4-(6-chloro-2-(methylthio)pyrimidin-4-yl)piperazine-1-carboxylateYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4,6-Dichloro-2-methylsulfanylpyrimidine (10 g) was dissolved in dichloromethane (200 ml) and triethylamine (20.6 g) was added. The mixture was stirred at room temperature and piperazine-1-carboxylic acid tert-butyl ester (9.54 g) was added in portions. The mixture was stirred at room temperature overnight. Mixture was washed with water (200 ml) then brine (100 ml). The organic layer was dried (MgSO4) then evaporated under reduced pressure to afford 4-(6-chloro-2-methylsulfanyl-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (17.9 g) as a white solid. 1H NMR (CDCl3): δ 6.11 (s, 1H), 3.58 (m, 4H), 3.44 (m, 4H), 2.42 (s, 3H), 1.41 (s, 9H).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. washMixture was washed with water (200 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-e91c6050139b4e0e8873e6b599397da0
Source dataset
uspto-grants-2008_02
Patent number
US07326715B2

Reaction notes

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