Azetidine → HCID 24954113, compound

HRID 386593Notes

Reaction equation

HRID 386593 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:5]=[C:4]([NH:15][C:16]2[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=2)[CH:3]=1.C([N:25]([CH2:29][CH3:30])[CH:26](C)C)(C)C.N1CCC1>C(O)CCC>[N:25]1([C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[Cl:14])[N:5]=[C:4]([NH:15][C:16]3[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=3)[CH:3]=2)[CH2:26][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 81531DiisopropylethylamineHCID 86638335HCID 86638335, compound

Product 1

HCID 24954113HCID 24954113, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
108 °C

Procedure

A mixture containing 6-chloro-2-(2-chlorophenyl)-N-(5-methyl-1H-pyrazol-3-yl)pyrimidin-4-amine (430 mg, 1.34 mmol), N,N-diisopropylethylamine (1.17 ml, 6.72 mmol), azetidine (272 mL, 4.03 mmol) and n-butanol (20 mL) was heated at 108° C. overnight. The reaction mixture was cooled to room temperature and concentrated in vacuo. The concentrate was treated with ethyl acetate/Petroleum ether and water and the resulting solid filtered. The solid was washed with further quantities of ethyl acetate/Petroleum ether and water and dried in vacuo to give the title compound as a white solid (350 mg, 76%). MS (ES+) m/e=341. 1H NMR: (DMSO) 2.28-2.40 (2H, m), 3.91-4.03 (4H, m), 5.90 (1H, brs), 6.30 (1H, brs), 7.31-7.60 (4H, m), 9.28 (1H, brs), 11.88 (1H, brs).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. additionThe concentrate was treated with ethyl acetate/Petroleum ether and water
  4. filtrationthe resulting solid filtered
  5. washThe solid was washed with further quantities of ethyl acetate/Petroleum ether and water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-de8417132f134f19a8853c09ce743640
Source dataset
uspto-grants-2013_02
Patent number
US08372850B2

Reaction notes

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