Diisopropylethylamine → Methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylate

HRID 16872

反応式

HRID 16872 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][O:13][CH2:14][CH:15]1[CH2:20][NH:19][CH2:18][CH2:17][NH:16]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH:15]1[NH:16][CH2:17][CH2:18][N:19]([C:2]2[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][N:3]=2)[CH2:20]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 12627752Methyl 2-chloropyrimidine-5-carboxylateHCID 142302642-(Methoxymethyl)piperazine

生成物 1

HCID 66589940Methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylate収率 75%

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 (300 mg, 1.74 mmol) in DCM (4.70 mL) was added to a stirred solution of 2-(methoxymethyl)piperazine (226 mg, 1.74 mmol) and N-ethyl-N-propan-2-ylpropan-2-amine (0.752 mL, 4.35 mmol) in DCM (4.00 mL) at 25° C. under nitrogen. The resulting solution was stirred at room temperature for 6 h. The reaction mixture was concentrated and diluted with MeOH. The resulting mixture was filtered. The filtrate was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford methyl 2-(3-(methoxymethyl)piperazin-1-yl)pyrimidine-5-carboxylate (346 mg, 75%) as a yellow solid. This was used directly with no further purification.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with MeOH
  3. filtrationThe resulting mixture was filtered
  4. customThe filtrate was purified by ion exchange chromatography
  5. washThe desired product was eluted from the column
  6. customwere evaporated to dryness

出典と根拠

ORDレコード
ord-80b8d9ce25f441588d5433e82862296a
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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