4-Chloro-2-methylthiopyrimidine → 1-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

HRID 1785464노트

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HRID 1785464 반응식
[C:1]1([C:7]2[CH:8]=[C:9]3[NH:14][CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Cl[C:71]1[CH:76]=[CH:75][N:74]=[C:73]([S:77][CH3:78])[N:72]=1>C1(C)C=CC=CC=1>[CH3:78][S:77][C:73]1[N:74]=[C:75]([N:14]2[CH2:13][CH2:12][CH2:11][N:10]3[C:15](=[O:17])[CH:16]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH:8]=[C:9]23)[CH:76]=[CH:71][N:72]=1

참가 물질

6

반응물 4

HCID 971134-Chloro-2-methylthiopyrimidineHCID 634876Binap, (A+-)-HCID 125016018-Phenyl-1,2,3,4-tetrahydropyrido[1,2-a]pyrimidin-6-oneHCID 23676156Sodium t-butoxide

생성물 1

HCID 575931211-(2-Methylsulfanyl-pyrimidin-4-yl)-8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
70 °C

실험 절차

To a mixture of 8-phenyl-1,2,3,4-tetrahydro-pyrido[1,2-a]pyrimidin-6-one (1.86 g, 8.23 mmol), sodium tert-butoxide (1.6 g, 16 mmol), BINAP (0.15 g, 0.207 mmol), and Pd (OAc)2 (55 mg, 0.2 mmol) was added toluene (20 mL) and 4-chloro -2-methylthiopyrimidine (1.5 mL, 12 mmol). After purged with N2 for 10 min, the overall mixture was heated at 70° C. for 3 h prior to being cooled to room temperature. The resulting material was diluted with saturated NHCl(aq), water, and DCM. The organic layer was taken and the aqueous layer was extracted with DCM. The combined organic layers were dried over Na2SO4, filtrated, and concentrated. Column chromatographic purification (3% MeOH in DCM) of the crude residue afforded the title compound as a yellow solid. MS m/e 351 (M+H)+.

후처리

  1. customAfter purged with N2 for 10 min
  2. temperatureto being cooled to room temperature
  3. additionThe resulting material was diluted with saturated NHCl(aq), water, and DCM
  4. extractionthe aqueous layer was extracted with DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltrated
  7. concentrationconcentrated
  8. customColumn chromatographic purification (3% MeOH in DCM) of the crude residue

출처 및 근거

ORD 기록
ord-4adc0ba0538a4090bb0ebdd5cc78d520
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07504403B2

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