Water → 2-[4-(2-Naphthalenylsulfonyl)-1-piperazinyl]-5-pyrimidinecarboxylic acid, ethyl ester

HRID 420437

반응식

HRID 420437 반응식
[H-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)(=[O:15])=[O:14].CS([C:26]1[N:31]=[CH:30][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:28][N:27]=1)(=O)=O.O>C1COCC1>[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:26]2[N:27]=[CH:28][C:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])=[CH:30][N:31]=2)[CH2:18][CH2:17]1)(=[O:15])=[O:14]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 254889Ethyl 2-(methylsulfonyl)pyrimidine-5-carboxylateHCID 7039571-(Naphthalene-2-sulfonyl)-piperazine

생성물 1

HCID 588449772-[4-(2-Naphthalenylsulfonyl)-1-piperazinyl]-5-pyrimidinecarboxylic acid, ethyl ester수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

NaH 60% (0.0217 mol) was added portionwise at room temperature to a solution of 1-(2-naphtalenesulfonyl)-piperazine (0.011 mol) in THF (50 ml) under N2 flow. The mixture was stirred at room temperature for 1 hour, then cooled to 0° C. A solution of 2-(methylsulfonyl)-5-pyrimidinecarboxylic acid, ethyl ester (0.014 mol) in THF (30 ml) was added quickly. The mixture was stirred at room temperature for 2 hours, poured out into water and extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was taken up in diethyl ether. The precipitate was filtered off and dried, yielding 3.92 g (84%) of 2-[4-(2-naphthalenylsulfonyl)-1-piperazinyl]- 5-pyrimidinecarboxylic acid, ethyl ester (interm. 8), melting point>260° C.

후처리

  1. temperaturecooled to 0° C
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. filtrationThe precipitate was filtered off
  9. customdried

출처 및 근거

ORD 기록
ord-31cdc26faeb24b9798653d469ea20653
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097611B2

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