Potassium Carbonate → (R)-7-ethyl-8-isopropyl-5-methyl-2-(2-phenyl-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

HRID 44845

반응식

HRID 44845 반응식
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7](=[O:13])[C@@H:6]([CH2:14][CH3:15])[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]=2[N:3]=1.[C:19]1([C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:14]([C@H:6]1[N:5]([CH:16]([CH3:18])[CH3:17])[C:4]2[N:3]=[C:2]([N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:11]=[CH:10][C:9]=2[N:8]([CH3:12])[C:7]1=[O:13])[CH3:15]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 695912-PhenylimidazoleHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 58405561(R)-2-Chloro-7-ethyl-8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydropyrimido[4,5-b]pyrazine

생성물 1

HCID 58405292(R)-7-ethyl-8-isopropyl-5-methyl-2-(2-phenyl-1H-imidazol-1-yl)-7,8-dihydropteridin-6(5H)-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
200 °C

실험 절차

A mixture of Intermediate C (100 mg, 0.37 mmol), 2-phenyl-1H-imidazole (533 mg, 3.7 mmol), Cut (35 mg, 0.18 mmol), trans-1,2-bis(methylamino)cyclo-hexane (52.5 mg, 0.07 mL, 0.37 mmol) and solid K2CO3 (511 mg, 3.7 mmol) in 2 mL of DMF was heated in a microwave reaction apparatus for 2 h at 200° C. After this time the reaction was transferred to a round bottom flask with the aid of EtOAc, then evaporated. The residue was purified by reverse-phase HPLC (PLRPS C-18 column, eluting with a gradient of 20-25% acetonitrile in water over 30 min) to give the title compound. LCMS: 377.2 m/z (M+H)+; ret. Time: 2.56 min (Analytical Method A); 1H NMR (400 MHz, CDCl3) δ: 7.9-7.8 (dd, 2H), 7.6-7.3 (m, 6H), 4.3 (dd, 1H), 3.8 (m, 1H), 3.4 (s, 3H), 1.9 (dd, 1H), 1.7 (dd, 1H), 1.05 (d, 3H), 0.9 (d, 3H) and 0.8 (d, 3H) ppm.

후처리

  1. customevaporated
  2. customThe residue was purified by reverse-phase HPLC (PLRPS C-18 column
  3. washeluting with a gradient of 20-25% acetonitrile in water over 30 min)

출처 및 근거

ORD 기록
ord-c7e167ee1ed040beb4e98960f186eb75
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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