Ethanol → HCID 178458594, compound

HRID 450405Notes

Reaction equation

HRID 450405 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([NH:17][C:18]3[CH:22]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[NH:20][N:19]=3)[C:14]([N+:27]([O-])=O)=[CH:13][N:12]=2)[CH3:9])=[N:6][CH:7]=1.[CH2:30](O)C.C(O)(=O)C.C(N)=N.C(OCC)(=O)C>[Cl-].[Na+].O.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]3[C:14]([N:27]=[CH:30][N:17]3[C:18]3[CH:22]=[C:21]([O:23][CH:24]([CH3:26])[CH3:25])[NH:20][N:19]=3)=[CH:13][N:12]=2)[CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 160693Formamidine acetateHCID 178458656HCID 178458656, compound2×

Product 1

HCID 178458594HCID 178458594, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

N2-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N4-(5-isopropoxy-1H-pyrazol-3-yl)-5-nitropyrimidine-2,4-diamine (Intermediate 31, 1.0 g) was dissolved into ethanol (20 mL) with Pd—C (150 mg) and a hydrogen inlet. The mixture was stirred at room temperature until no starting material was detected with TLC or LCMS. Formamidine acetate (1.0 g) was added to the filtrate after the filtration of resulting mixture. The mixture was stirred at 85° 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 0.7 g desired product. MS (electrospray): 383 (M+1) for C18H19FN8O. 1H NMR (300 MHz, CD3OD) δ ppm 8.70 (s, 1H) 8.40 (m, 2H) 7.50 (dd, 2H) 6.00 (s, 1H) 5.20 (m, 1H) 4.20 (m, 1H) 1.50 (d, 3H) 1.40 (d, 6H).

Workup

  1. filtrationafter the filtration
  2. customof resulting mixture
  3. stirringThe mixture was stirred at 85° 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)

Sources & evidence

ORD record
ord-b3ee76687cb64f8085f5e0dc947c945d
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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