Sodium Hydroxide → HCID 59421144, 화합물

HRID 883009노트

반응식

HRID 883009 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([C:14]([O:16]CC)=O)=[CH:12][N:11]=[C:10]([S:19][CH3:20])[N:9]=1.[OH-].[Na+].C(Cl)(=O)C(Cl)=O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=1)[CH2:34][NH:35][CH:36]([CH3:38])[CH3:37].C(N(C(C)C)CC)(C)C>C(O)C.O.C(Cl)Cl.CN(C=O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=1)[CH2:34][N:35]([CH:36]([CH3:38])[CH3:37])[C:14]([C:13]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[N:9][C:10]([S:19][CH3:20])=[N:11][CH:12]=1)=[O:16]

참가 물질

10

반응물 5

HCID 14798Sodium HydroxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 17156044N-[(3-Methoxyphenyl)methyl]propan-2-amineHCID 59421256Ethyl 4-(2-fluorophenyl)-2-(methylthio)-5-pyrimidinecarboxylate

생성물 1

HCID 59421144HCID 59421144, 화합물수율 23.5%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매3회

실험 절차

A mixture of ethyl 4-(2-fluorophenyl)-2-(methylthio)pyrimidine-5-carboxylate (3.3 g, 10.96 mmol), solid NaOH (3.2 g) in ethanol (30 mL) and water (6 mL) was refluxed for 1 h. and cooled to room temperature. The solvent was removed under reduced pressure, and the residue was acidified with 6N HCl. The product was extracted with EtOAC (3×50 mL), and the organic extracts were dried and concentrated to give crude acids (1.6 g). A solution of 2 M oxalyl chloride in CH2Cl2 (3.00 mL, 6 mmol) was added to a stirred solution of the crude acids (1.6 g) in CH2Cl2 (25 mL) and DMF (1 mL) at room temperature, and stirring continued for 15 min. A solution of N-(3-methoxybenzyl)propan-2-amine, (1.07 g, 6.00 mmol) in CH2Cl2 (2 mL) and diisopropylethylamine (2 mL, 12 mmol) was added and stirred for 1 hr. The solvent was removed under reduced pressure and the residue was purified by Biotage SP1 on packed silica gel column (10%-80% EtOAc/Hexanes gradient) to give N-(3-methoxybenzyl)-4-(2-fluorophenyl)-N-isopropyl-2(methylthio)pyrimidine-5-carboxamide (0.6 g, 13%). Mass Spec. FIA MS 426 (M+1).

후처리

  1. temperaturewas refluxed for 1 h.
  2. customThe solvent was removed under reduced pressure
  3. extractionThe product was extracted with EtOAC (3×50 mL)
  4. customthe organic extracts were dried
  5. concentrationconcentrated
  6. customto give crude acids (1.6 g)
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by Biotage SP1

출처 및 근거

ORD 기록
ord-6e54520e814946a4adf666dafde522b2
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236815B2

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