Bromine → 8-Cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester

HRID 1989019

반응식

HRID 1989019 반응식
BrBr.[CH2:3]([O:5][C:6]([CH:8]1[CH2:19][N:18]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:11]2[N:12]=[C:13]([S:16][CH3:17])[N:14]=[CH:15][C:10]=2[C:9]1=[O:26])=[O:7])[CH3:4].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH2:3]([O:5][C:6]([C:8]1[C:9](=[O:26])[C:10]2[CH:15]=[N:14][C:13]([S:16][CH3:17])=[N:12][C:11]=2[N:18]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[CH:19]=1)=[O:7])[CH3:4]

참가 물질

5

반응물 3

HCID 24408BromineHCID 81531DiisopropylethylamineHCID 68583787HCID 68583787, 화합물

생성물 1

HCID 685832078-Cyclohexyl-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester수율 102%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Bromine (0.15 g, 0.94 mmol) was added to a solution of 8-cyclohexyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.28 g, 0.79 mmol) in DCM (10 mL). After 5 min, the solution was concentrated and the crude residue was redissolved in DCM (10 mL) and diisopropylethylamine (0.42 mL, 2.4 mmol) was added. After 15 h, the reaction mixture was partitioned between water and DCM, the organic layer was separated, dried (MgSO4) and concentrated to provide 0.28 g (87%) of the title compound.). Mass Spectrum (LCMS, ESI pos.) Calcd. For C17H21N3O3S: 347.13, found: (M+H) 348.3.

후처리

  1. concentrationthe solution was concentrated
  2. dissolutionthe crude residue was redissolved in DCM (10 mL)
  3. waitAfter 15 h
  4. customthe reaction mixture was partitioned between water and DCM
  5. customthe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b55581d20b1647ecaa07731a46ce3aaf
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642270B2

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