Diethyl Ether → 1-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl ester

HRID 216268Notes

Reaction equation

HRID 216268 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[CH2:12][CH2:11]2)[CH:3]=1.[N+](=[CH2:21])=[N-].C(OCC)C>CO.C1(C)C=CC=CC=1>[CH3:21][O:17][C:16]([CH:13]1[CH2:14][CH2:15][N:10]([C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([O:8][CH3:9])[N:5]=2)[CH2:11][CH2:12]1)=[O:18]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 862401201-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid

Product 1

HCID 866157151-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl esterYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 1-(6-chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid [131 mg, 0.48 mmol] in MeOH (1 mL) and toluene (1 mL) is added a solution of 2 M diazomethane in diethylether (0.48 mL, 0.96 mmol). The solution is stirred for 2 h at ambient temperature and concentrated. The residue is subjected to chromatography on silica gel eluting with 40% ethyl acetate:heptane to afford 1-(6-chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid methyl ester [103 mg, 75%] as a solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0beba40f805343faa90c2d864da08ded
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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