Diisopropylethylamine → 4-[2-Amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester

HRID 510469ノート

反応式

HRID 510469 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=1.C(N(CC)C(C)C)(C)C.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>O1CCOCC1>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][N:32]([C:6]2[C:5]([NH:9][CH:10]=[O:11])=[C:4]([Cl:12])[N:3]=[C:2]([NH2:1])[N:7]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 10198177N-(2-Amino-4,6-dichloropyrimidin-5-yl)formamide

生成物 1

HCID 895615864-[2-Amino-6-chloro-5-(formylamino)pyrimidin-4-yl]piperazine-1-carboxylic acid tert-butyl ester収率 100%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
55 °C

実験手順

To a suspension of N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (10.0 g, 48.3 mmol) in 1,4-dioxane (400 mL) were added N,N-diisopropylethylamine (12.7 mL, 72.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (9.8 g, 53.1 mmol). The mixture was stirred at 55° C. for 1 h. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The aqueous phase was extracted with further DCM and the combined organic fractions were washed with brine, then dried (Na2SO4) and evaporated in vacuo to give the title compound (17.1 g, 100%) as a white solid. LCMS (ES+) 357.4 (M+H)+, RT 1.08 minutes (method 3).

後処理

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between DCM and water
  3. extractionThe aqueous phase was extracted with further DCM
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-50144f96d0134c90aa3a2851be357580
出典データセット
uspto-grants-2015_08
特許番号
US09096614B2

反応ノート

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