2-Chloro-4,6-dimethylpyrimidine → HCID 67342807, compound

HRID 2264415Notes

Reaction equation

HRID 2264415 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(N(C(C)C)C(C)C)C>C(#N)C.CC(N(C)C)=O>[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:2]2[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 205502-Chloro-4,6-dimethylpyrimidineHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 67342807HCID 67342807, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of 2-chloro-4,6-dimethyl-pyrimidine (1.50 g, 10.52 mmol, 1.0 equiv; commercially available), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (2.53 g, 12.62 mmol, 1.2 equiv; commercially available) and N-ethyl diisopropylamine (2.15 mL, 1.63 g, 12.62 mmol, 1.2 equiv) in acetonitrile (8 mL) and DMAc (2 mL) was heated by microwave irradiation to 160° C. for 1 h and then to 180° C. for 30 min. The reaction mixture was concentrated under reduced pressure and the crude material purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 1.47 g (46%) of the title compound. MS (ISP): 307.5 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude material purified by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate providing 1.47 g (46%) of the title compound

Sources & evidence

ORD record
ord-75f058fe9e364f42901ce7c5af6714e6
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

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