Morpholine → N-(5-Methyl-1H-pyrazol-3-yl)-2-(methylthio)-6-morpholin-4-yl-5-nitropyrimidin-4-amine

HRID 450392

반응식

HRID 450392 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[N:5]=[C:4]([S:12][CH3:13])[N:3]=1.[CH3:14][C:15]1[NH:19][N:18]=[C:17]([NH2:20])[CH:16]=1.CCN(C(C)C)C(C)C.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C1COCC1.O.CCOC(C)=O>[CH3:14][C:15]1[NH:19][N:18]=[C:17]([NH:20][C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)[N:5]=[C:4]([S:12][CH3:13])[N:3]=2)[CH:16]=1

참가 물질

8

반응물 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 113454584,6-Dichloro-2-(methylthio)-5-nitropyrimidine2회

생성물 1

HCID 68734536N-(5-Methyl-1H-pyrazol-3-yl)-2-(methylthio)-6-morpholin-4-yl-5-nitropyrimidin-4-amine

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine (Intermediate 56, 820 mg) in THF at 0° C. were added 5-methyl-1H-pyrazol-3-amine (350 mg) and DIPEA (1.6 ml) drop-wise. The resulting mixture was stirred at this temperature for 3 hours whereupon morpholine (1 ml) was added. The resulting mixture was allowed to warm to ambient temperature over 10 hours. The mixture was diluted with H2O and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, saturated NaHCO3 (aq) solution, dried and evaporation of the volatiles under reduced pressure gave a colored residue. Purification by column chromatography (50% EtOAc/hexanes) gave the title compound (820 mg). LCMS: 352 [M+1].

후처리

  1. additionwas added
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine, saturated NaHCO3 (aq) solution
  4. customdried
  5. customevaporation of the volatiles under reduced pressure
  6. customgave a colored residue
  7. customPurification by column chromatography (50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-0e93f9d296b14d52880e09c304f1e6b5
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486966B2

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