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 1045691ノート

反応式

HRID 1045691 の反応式
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]

参加物

5

反応物 3

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

生成物 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 ester収率 74.4%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-df6a4fdb67654ebc8cd50310dd9a758f
出典データセット
uspto-grants-2013_10
特許番号
US08569294B2

反応ノート

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