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Water → (S)-1-(2-(2,6-dimethylphenyl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

HRID 80775
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HRID 80775 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([N:19]2[CH2:24][CH2:23][C@H:22]([O:25][CH3:26])[C:21]([CH3:28])([CH3:27])[CH2:20]2)[C:12]2[CH2:18][NH:17][CH2:16][CH2:15][C:13]=2[N:14]=1.CCC(O[C:34]([CH:36]([CH3:38])[CH3:37])=[O:35])=O.[C:39]1([CH3:45])C=CC=CC=1.[OH2:46]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[N:10]=[C:11]([N:19]2[CH2:24][CH2:23][C@H:22]([O:25][CH3:26])[C:21]([CH3:28])([CH3:27])[CH2:20]2)[C:12]2[CH2:18][N:17]([C:39](=[O:46])[CH2:45][C:34](=[O:35])[CH:36]([CH3:37])[CH3:38])[CH2:16][CH2:15][C:13]=2[N:14]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 1140TolueneHCID 22025518HCID 22025518, 화합물HCID 89686034(S)-2-(2,6-dimethylphenyl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 89397283(S)-1-(2-(2,6-dimethylphenyl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione

시약·촉매·용매

2
HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

반응 조건

온도
150 °C

실험 절차

In a microwave reaction vial (S)-2-(2,6-dimethylphenyl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (115 mg, 0.302 mmol), prepared by a method similar to that described by Examples 21-c and 21-d, was combined with methyl isobutyryl acetate (65 mg, 0.45 mmol), toluene (2 mL) and DMAP (7 mg, 0.060 mmol). The vial was heated in a microwave reactor at 150° C. for 30 min. The reaction mixture was then diluted with DCM and water. The layers were separated and the aqueous phase was extracted twice with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by silica gel flash column chromatography (0-100% 10:1 EtOAc:MeOH/heptanes) to provide (S)-1-(2-(2,6-dimethylphenyl)-4-(4-methoxy-3,3-dimethylpiperidin-1-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione. MS (ESI+) m/z 493.0 (M+H)+

후처리

  1. customprepared by a method similar to
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted twice with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by silica gel flash column chromatography (0-100% 10:1 EtOAc:MeOH/heptanes)

출처 및 근거

ORD 기록
ord-526c61b65e0e4ccb9806f191750e148b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846656B2

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