Cesium carbonate → (4-Trifluoromethyl-phenyl)-[2-(2-triisopropylsilanylsulfanyl-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-amine

HRID 60208

반응식

HRID 60208 반응식
I[C:2]1[CH:28]=[CH:27][CH:26]=[CH:25][C:3]=1[CH2:4][C:5]1[S:6][C:7]2[N:8]=[CH:9][N:10]=[C:11]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=3)[C:12]=2[N:13]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH:54]([Si:57]([CH:62]([CH3:64])[CH3:63])([CH:59]([CH3:61])[CH3:60])[SH:58])([CH3:56])[CH3:55]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[F:22][C:21]([F:24])([F:23])[C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:11]2[C:12]3[N:13]=[C:5]([CH2:4][C:3]4[CH:25]=[CH:26][CH:27]=[CH:28][C:2]=4[S:58][Si:57]([CH:59]([CH3:61])[CH3:60])([CH:62]([CH3:64])[CH3:63])[CH:54]([CH3:55])[CH3:56])[S:6][C:7]=3[N:8]=[CH:9][N:10]=2)=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 3435097Tris(propan-2-yl)silanethiolHCID 42622946[2-(2-Iodo-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine

생성물 1

HCID 42641810(4-Trifluoromethyl-phenyl)-[2-(2-triisopropylsilanylsulfanyl-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-amine수율 60%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

[2-(2-Iodo-benzyl)-thiazolo[5,4-d]pyrimidin-7-yl]-(4-trifluoromethyl-phenyl)-amine (0.26, 0.50 mmol), palladium acetate (5.7 mg, 0.03 mmol), PPh3 (0.03 g, 0.10 mmol), and Cs2CO3 (0.21 g, 0.65 mmol) were combined in a sealed tube and placed under N2 atmosphere. Toluene (5 mL) was added followed by triisopropylsilanethiol (0.11, 0.55 mmol) and the resulting suspension was heated to 100° C. for 8 h. The reaction mixture was cooled to rt and filtered through a pad of diatomaceous earth. The filtrate was concentrated and purified by FCC to provide the title compound as a colorless solid (0.15 g, 60%). MS (ESI): mass calcd. for C28H33F3N4S2Si, 574.8; m/z found, 575.2 [M+H]+. 1H NMR (CDCl3): 8.65-8.60 (m, 1H), 8.14 (s, 1H), 7.99 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.6 Hz, 2H), 7.57-7.53 (m, 1H), 7.35-7.32 (m, 1H), 7.25-7.18 (m, 2H), 4.79 (s, 2H)

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. filtrationfiltered through a pad of diatomaceous earth
  3. concentrationThe filtrate was concentrated
  4. custompurified by FCC

출처 및 근거

ORD 기록
ord-b54888de536b4155932c18fb15eb1aff
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440978B2

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