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Ethanol → 9-(5-Cyclopropyl-1H-pyrazol-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-9H-purin-2-amine

HRID 450399
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HRID 450399 반응식
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][N:13]=[C:12]([NH:19][C@H:20]([C:22]4[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=4)[CH3:21])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[CH2:29](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([N:9]3[CH:29]=[N:16][C:15]4[C:10]3=[N:11][C:12]([NH:19][C@H:20]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][N:23]=3)[CH3:21])=[N:13][CH:14]=4)[CH:5]=2)[CH2:3][CH2:2]1
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참가 물질

7

반응물 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 86649278N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-5-nitropyrimidine-2,4-diamine2회

생성물 1

HCID 251159669-(5-Cyclopropyl-1H-pyrazol-3-yl)-N-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-9H-purin-2-amine

시약·촉매·용매 2

HCID 23938Palladium촉매
HCID 57417360Sodium chloride; water용매

실험 절차

N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-5-nitropyrimidine-2,4-diamine (Intermediate 19, 0.25 g) was dissolved into ethanol (20 mL) with Pd—C (40 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (0.5 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 95° C. for 4 hours. Ethyl acetate (40 mL) was added into the resulting mixture, and brine (10 mL×3) was used to wash the organic layer. The organic layer was dried and concentrated. The resulting residue was separated by silica gel column (Ethyl acetate/MeOH) to afford 0.03 g of the title compound. MS (electrospray): 365 (M+1) for C18H17FN8. 1H NMR (300 MHz, CD3OD) δ ppm 8.70 (s, 2H) 8.55 (s, 1H) 8.50 (s, 1H) 7.50 (d, 2H) 6.30 (br, 1H) 5.20 (dd, 1H) 2.00 (m, 1H) 1.65 (d, 3H) 1.10 (m, 2H) 0.90 (m, 2H).

후처리

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 95° C. for 4 hours
  4. washto wash the organic layer
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe resulting residue was separated by silica gel column (Ethyl acetate/MeOH)

출처 및 근거

ORD 기록
ord-22e79c02c1d246e68a0d3c38f3619a10
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08486966B2

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