Triethylamine → (3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1045691Notes

Reaction equation

HRID 1045691 reaction equation
Cl[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[N:3]=1.[CH3:16][C@H:17]1[NH:22][CH2:21][CH2:20][N:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:18]1.C(N(CC)CC)C>CN1CCCC1=O>[C:26]([O:25][C:23]([N:19]1[CH2:20][CH2:21][N:22]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[CH:5]=[C:4]([C:10]3[CH:15]=[CH:14][N:13]=[CH:12][N:11]=3)[N:3]=2)[C@H:17]([CH3:16])[CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 179544602-Chloro-3-methyl-6-(pyrimidin-4-YL)pyrimidin-4-one

Product 1

HCID 57870141(3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4']bipyrimidinyl-2-yl)-piperazine-1-carboxylic acid tert-butyl esterYield 74.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 2-chloro-3-methyl-6-(pyrimidin-4-yl)-3H-pyrimidin-4-one (5.3 g, 24 mmol), tert-butyl (3R)-3-methylpiperazine-1-carboxylate (5.0 g, 25 mmol) and triethylamine (7.6 g, 75 mmol) in N-methyl-2-pyrrolidone (25 ml) was stirred for 6 hours at 90° C. The solution was partitioned between water and ethyl acetate, and the organic layer was washed with water, brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; ethyl acetate) to afford (3R)-3-methyl-4-(1-methyl-6-oxo-1,6-dihydro-[4,4′]bipyrimidinyl-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (6.9 g, 71%).

Workup

  1. customThe solution was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; ethyl acetate)

Sources & evidence

ORD record
ord-df6a4fdb67654ebc8cd50310dd9a758f
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

Loading…