Diisopropylethylamine → Methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate

HRID 16906

反応式

HRID 16906 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=1.[CH3:12][N:13]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:12][N:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:15][CH2:14]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 2283491-MethylhomopiperazineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylate

生成物 1

HCID 66589654Methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate収率 94.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of methyl 2-chloropyrimidine-5-carboxylate (200 mg, 1.16 mmol) in dichloromethane (4.00 mL) was added to a stirred solution of 1-methyl-1,4-diazepane (0.144 mL, 1.16 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.902 mL, 5.22 mmol) in dichloromethane (4.00 mL) at 25° C. The resulting solution was stirred at ambient temperature for 18 h. The reaction mixture was evaporated to dryness and redissolved in MeOH (20 mL) and the crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford methyl 2-(4-methyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (274 mg, 94%) as a white solid. This was used directly with no further purification.

後処理

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionredissolved in MeOH (20 mL)
  3. customthe crude product was purified by ion exchange chromatography
  4. washThe desired product was eluted from the column
  5. customevaporated to dryness

出典と根拠

ORDレコード
ord-4ab41f61fa5e4209bcc6a4c7197a6667
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

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