Diisopropylethylamine → 2-(1-tert-Butoxycarbonyl-piperidin-4-ylamino)-pyrimidine-4-carboxylic acid methyl ester

HRID 2264420Notes

Reaction equation

HRID 2264420 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[N:6]=1)=[O:4].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([NH2:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(C(C)C)C(C)C)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([NH:25][CH:22]2[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[CH2:24][CH2:23]2)[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 43811076Methyl 2-chloropyrimidine-4-carboxylate

Product 1

HCID 687827492-(1-tert-Butoxycarbonyl-piperidin-4-ylamino)-pyrimidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-pyrimidine-4-carboxylic acid methyl ester (0.62 g, 3.59 mmol, 1.0 equiv), 4-amino-piperidine-1-carboxylic acid tert-butyl ester (0.86 g, 4.31 mmol, 1.2 equiv; commercially available) and N-ethyl diisopropylamine (0.73 mL, 0.56 g, 4.31 mmol, 1.2 equiv) in acetonitrile (60 mL) was heated by microwave irradiation to 110° C. After stirring for 40 min, the reaction mixture was concentrated under reduced pressure and the residue purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate providing 0.48 g (34%) of the title compound. MS (ISP): 337.5 [M+H]+.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue purified by silica column chromatography
  3. washeluting with a gradient of heptane/ethyl acetate providing 0.48 g (34%) of the title compound

Sources & evidence

ORD record
ord-1771c3994fa2438483417ece9f6369d0
Source dataset
uspto-grants-2010_12
Patent number
US07855194B2

Reaction notes

Loading…