Triethylamine → 4-Methylbenzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate

HRID 1827174Notes

Reaction equation

HRID 1827174 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[N:22]1[CH:23]=[CH:24][CH:25]=[N:26][C:21]=1[NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 744042-ChloropyrimidineHCID 161094174-Methylbenzyl 4-(aminomethyl)1-piperidinecarboxylate2×

Product 1

HCID 98810904-Methylbenzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 4-methylbenzyl 4-(aminomethyl)-1-piperidinecarboxylate (INTERMEDIATE 2A) (20.00 g, 76.23 mmol), 2-chloro-pyrimidine (8.73 g, 76.23 mmol) and triethylamine (21.25 mL, 152.46 mmol) in DMF (40 mL) was heated at 100° C. for 6 h. The reaction solution was cooled to rt, then diluted with ethyl acetate (800 mL), washed with sat. aq. NaHCO3 (100 mL), water (3×100 mL), brine (100 mL), dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (CH2Cl2/IPA/hexanes) to give 4-methylbenzyl 4-[(2-pyrimidinylamino)methyl]-1-piperidinecarboxylate. M.S.(M+1): 341.30.

Workup

  1. washwashed with sat. aq. NaHCO3 (100 mL), water (3×100 mL), brine (100 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (CH2Cl2/IPA/hexanes)

Sources & evidence

ORD record
ord-f6e00a4435814afbb32ce1e01f3bc286
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

Loading…