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Cesium carbonate → HCID 86686649, 화합물

HRID 1850609
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HRID 1850609 반응식
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[N:14]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[C:8]2[N:9]=[C:10](Cl)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4].[C:21](=[NH:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:35]([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].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>[CH3:20][N:2]([CH3:1])[C:3]([C:5]1[N:14]([CH:15]([CH2:16][CH3:35])[CH2:19][CH2:18][CH3:17])[C:8]2[N:9]=[C:10]([N:34]=[C:21]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:11]=[CH:12][C:7]=2[CH:6]=1)=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 583154322-Chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

생성물 1

HCID 86686649HCID 86686649, 화합물수율 80%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매
HCID 634876
Binap, (A+-)-
촉매
HCID 312751,4-Dioxane용매

반응 조건

온도
120 °C

실험 절차

To a suspension of 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (2.93 g, 10 mmol) in 50 mL Dioxane were added benzophenone imine (1.90 g, 10.5 mmol), Pd(OAc)2 (0.11 g, 0.5 mmol), BINAP (0.31 g, 0.5 mmol) and Cs2CO3 (4.89 g, 15 mmol) and the flask was purged with N2. Then the tube was sealed and the mixture was heated for 1 h at 120° C. Then the suspension was added with heptane and filtered. The precipitate was extracted with DCM and the extract was purified by SiO2 column chromatography to give 2-(benzhydrylidene-amino)-7-(1-ethyl-butyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (3.5 g, 8.0 mmol, 80% yield). MS m/z 438.5 (M+H)+.

후처리

  1. customthe flask was purged with N2
  2. customThen the tube was sealed
  3. additionThen the suspension was added with heptane
  4. filtrationfiltered
  5. extractionThe precipitate was extracted with DCM
  6. customthe extract was purified by SiO2 column chromatography

출처 및 근거

ORD 기록
ord-7d1cb9458e2d42859b2abe13e5f0e9cb
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08957074B2

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