1,1-dimethylethyl (2S)-2-[(3-chloro-7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate → 3-chloro-7-methyl-2-[(2S)-2-piperidinylmethyl]imidazo[1,2-a]pyrimidine

HRID 418043Notes

Reaction equation

HRID 418043 reaction equation
[Cl:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]2=[N:4][C:3]=1[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][N:14]1C(OC(C)(C)C)=O>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:5]2=[N:4][C:3]=1[CH2:12][C@@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][NH:14]1

Participants

4

Reactant 1

HCID 593767001,1-dimethylethyl (2S)-2-[(3-chloro-7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate

Product 1

HCID 593766993-chloro-7-methyl-2-[(2S)-2-piperidinylmethyl]imidazo[1,2-a]pyrimidineYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S)-2-[(3-chloro-7-methylimidazo[1,2-a]pyrimidin-2-yl)methyl]-1-piperidinecarboxylate (D4) (0.085 g, 0.23 mmol) in DCM (2 ml), TFA (0.5 ml) was added dropwise at 0° C. and the solution was stirred for 1 h. The solvent was removed and the residue charged into a SCX column and eluted with methanol and ammonia 2 M in methanol. Collected fractions gave the title compound (0.060 g, 0.23 mmol, 97% yield) as a colorless oil. UPLC: rt=0.39, peak observed: 265 (M+1, 100%) and 267 (M+1, 33%). C13H17ClN4 requires 265. 1H NMR (400 MHz, CDCl3) δ(ppm): 8.12-8.21 (d, 1H), 6.80-6.88 (d, 1H), 3.02-3.14 (m, 2H), 2.78 2.91 (m, 2H), 2.60-2.72 (m, 4H), 1.28-1.84 (m, 6H).

Workup

  1. customThe solvent was removed
  2. additionthe residue charged into a SCX column
  3. washeluted with methanol and ammonia 2 M in methanol

Sources & evidence

ORD record
ord-2b75b62bb21b484886763bd46a58d388
Source dataset
uspto-grants-2012_01
Patent number
US08093255B2

Reaction notes

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