Triethylamine → HCID 25002829, compound

HRID 1045684Notes

Reaction equation

HRID 1045684 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:15]1[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[N:16]=1.C(N(CC)CC)C>>[CH2:1]([O:8][CH:9]1[CH2:13][CH2:12][N:11]([C:15]2[N:20]([CH3:21])[C:19](=[O:22])[CH:18]=[C:17]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[N:16]=2)[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 112760814(3H)-Pyrimidinone, 2-chloro-3-methyl-6-(4-pyridinyl)-HCID 144973533-(Benzyloxy)pyrrolidine

Product 1

HCID 25002829HCID 25002829, compoundYield 70%

Procedure

A solution of 3-benzyloxypyrrolidine (182 mg, 1.03 mmol), 2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (181 mg, 0.82 mmol) and triethylamine (387 mmol, 3.83 mmol) was refluxed for 3 hours. After removal of the solvent, the residue was purified by silica gel column chromatography (eluent; dichloromethane/ethanol=10/1) and washed with ethyl acetate to afford 2-(3-benzyloxy-pyrrolidin-1-yl)-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (208 mg, 70%).

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel column chromatography (eluent; dichloromethane/ethanol=10/1)
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ca1f8ed1bdd749368f8fcca34a462208
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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