Water → tert-Butyl (1-(6-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)carbamate

HRID 451500Notes

Reaction equation

HRID 451500 reaction equation
ClC1C=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][N:3]=1.[C:12]([N:19]1CCC(N)C[CH2:20]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].[CH3:26][CH2:27][N:28]([CH:32]([CH3:34])C)[CH:29]([CH3:31])C.O>CN1C(=O)CCC1>[F:11][C:8]([F:9])([F:10])[C:6]1[N:5]=[CH:4][N:3]=[C:32]([N:28]2[CH2:27][CH2:26][CH:20]([NH:19][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:31][CH2:29]2)[CH:34]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 115428814-Chloro-6-(trifluoromethyl)pyrimidine

Product 1

HCID 67344970tert-Butyl (1-(6-(trifluoromethyl)pyrimidin-4-yl)piperidin-4-yl)carbamateYield 92%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a mixture of 4-chloro-6-(trifluoromethyl)pyrimidine (0.82 g, 4.49 mmol) and Boc-4-aminopiperidine (1.17 g, 5.84 mmol) in NMP (5.7 mL) was added DIPEA (1.10 mL, 6.29 mmol) and after 30 minutes the mixture was poured into water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 70 g, 0 to 50% ethyl acetate in heptane) afforded the title compound (1.43 g, 92%) as a white solid. MS ISP (m/e): 347.2 [(M+H)+].

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customPurification by chromatography (silica gel, 70 g, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-f737b133ce1a412cb3d11329a82beb71
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

Loading…