Hydrogen Peroxide → HCID 58169130, compound

HRID 1484854Notes

Reaction equation

HRID 1484854 reaction equation
[OH:1]O.[CH:3]1([C:6]2[N:10](C(=O)C)[N:9]=[C:8]([NH:14][C:15]3[C:20](B4OC(C)(C)C(C)(C)O4)=[CH:19][N:18]=[C:17]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:16]=3)[CH:7]=2)[CH2:5][CH2:4]1.O>C1COCC1>[CH:3]1([C:6]2[NH:10][N:9]=[C:8]([NH:14][C:15]3[C:20]([OH:1])=[CH:19][N:18]=[C:17]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[N:16]=3)[CH:7]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 58169478HCID 58169478, compound

Product 1

HCID 58169130HCID 58169130, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30% H2O2 (10 mL) was added to the solution of 1-(5-cyclopropyl-3-(2-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-4-ylamino)-1H-pyrazol-1-yl)ethanone (200 mg, 0.45 mmol, 1.0 eq) in THF (5 mL) at 0° C. The mixture was stirred for 1 h and water was added. The solid was collected and dissolved in methanol (8 mL). To the solution was added 5 N NaOH (4 mL). The mixture was stirred for 2 h at room temperature and concentrated. To the residue was added ethanol and EtOAc. The emerged solid was filtered off. The filtrate was concentrated and the residue was recrystallized with CH2Cl2 and ethyl ether to give 4-(5-cyclopropyl-1H-pyrazol-3-ylamino)-2-phenylpyrimidin-5-ol (Compound 55) (10 mg, 8% over 2 steps). LC-MS (m/z)=294.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6): δ 0.69-0.74 (m, 2H), 0.93-0.98 (m, 2H), 1.85-1.89 (m, 1H), 6.52 (bs, 1H), 7.40-7.47 (m, 3H), 7.93 (s, 1H), 8.22 (d, J=7.6 Hz, 2H), 8.41 (bs, 1H), 10.43 (bs, 1H), 12.09 (bs, 1H).

Workup

  1. customThe solid was collected
  2. dissolutiondissolved in methanol (8 mL)
  3. additionTo the solution was added 5 N NaOH (4 mL)
  4. stirringThe mixture was stirred for 2 h at room temperature
  5. concentrationconcentrated
  6. additionTo the residue was added ethanol and EtOAc
  7. filtrationThe emerged solid was filtered off
  8. concentrationThe filtrate was concentrated
  9. customthe residue was recrystallized with CH2Cl2 and ethyl ether

Sources & evidence

ORD record
ord-f18fdbbcf24e402b8c03f88ce53957f4
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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