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

HRID 510469노트

반응식

HRID 510469 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
55 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50144f96d0134c90aa3a2851be357580
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096614B2

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