Methanol → HCID 67059565, compound

HRID 600431Notes

Reaction equation

HRID 600431 reaction equation
[N:1]1([C:10]2[N:15]=[C:14]([NH:16][CH:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)[C:13]([N+:23]([O-])=O)=[C:12]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[O-]S(S([O-])=O)=O.[Na+].[Na+].C([O-])(O)=O.[Na+].CO>C1COCC1.O.C(OCC)(=O)C>[N:1]1([C:10]2[N:15]=[C:14]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)[C:13]([NH2:23])=[C:12]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

8

Reactant 4

HCID 887MethanolHCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 57612659HCID 57612659, compound

Product 1

HCID 67059565HCID 67059565, compoundYield 70.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 48 mg (0.11 mmol) of 2-(1H-benzo[d]imidazol-1-yl)-5-nitro-6-phenyl-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine in 10 mL THF was added a solution of 300 mg Na2S2O4 and 100 mg NaHCO3 in 30 mL of water, followed by 2 mL of methanol. The reaction mixture was stirred at room temperature (HPLC monitoring). Upon completion of the reaction, the mixture was diluted with 70 mL of ethyl acetate, the layers were separated, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine, dried (anhydrous MgSO4), and the solvent removed in vacuo to give 30 mg (68% yield) of desired product, which was used in the next step without further purification. MS (EI) m/z 387.4 (MH)+.

Workup

  1. customUpon completion of the reaction
  2. customthe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (anhydrous MgSO4)
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-23ea8826bc99475dba508ad307626149
Source dataset
uspto-grants-2011_03
Patent number
US07902187B2

Reaction notes

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