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 1785464

反応式

HRID 1785464 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-4adc0ba0538a4090bb0ebdd5cc78d520
出典データセット
uspto-grants-2009_03
特許番号
US07504403B2

関連ノート

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