Methanol → HCID 66970494, compound

HRID 1363153Notes

Reaction equation

HRID 1363153 reaction equation
[N:1]1([C:10]2[N:15]=[C:14]([NH:16][C@H:17]3[CH2:22][CH2:21][O:20][CH2:19][C@H:18]3[CH3:23])[C:13]([N+:24]([O-])=O)=[CH:12][N:11]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].CO>C1COCC1.O.CCOC(C)=O>[N:1]1([C:10]2[N:15]=[C:14]([NH:16][C@H:17]3[CH2:22][CH2:21][O:20][CH2:19][C@H:18]3[CH3:23])[C:13]([NH2:24])=[CH:12][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 66970519HCID 66970519, compound

Product 1

HCID 66970494HCID 66970494, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(1H-benzo[d]imidazol-1-yl)-N-(cis-3-methyl-tetrahydro-2H-pyran-4-yl)-5-nitropyrimidin-4-amine (51 mg) in THF (10 mL) was added a solution of sodium hydrosulfite (300 mg) and sodium bicarbonate (150 mg) in water (10 mL). The mixture briefly became blue followed by colorless. Methanol (1 mL) was added to maintain the homogeneity of the solution. The mixture was diluted with 70 mL EtOAc and washed twice with brine. The aqueous washes were extracted with another 50 mL of EtOAc and then the combined organic layers were dried over sodium sulfate and concentrated in vacuo to provide 2-(1H-benzo[d]imidazol-1-yl)-N4-(cis-3-methyl-tetrahydro-2H-pyran-4-yl)pyrimidine-4,5-diamine. The diamine intermediate was dissolved in THF (5 mL) and treated with 1,1′-carbonyldiimidazole (80 mg) at 50° C. for 16 hours. The mixture was diluted with 50 mL EtOAc and washed 3 times with brine. The organic layer was separated, dried over sodium sulfate, and concentrated in vacuo. Column chromatography (2→4% MeOH/DCM) provided 19.3 mg of the title compound. 1H-NMR (300 MHz, 5% CD3OD in CDCl3) δ 8.9 (s, 1H), 8.5 (d, 1H), 8.2 (s, 1H), 7.8 (d, 1H), 7.4 (t, 1H), 7.3 (t, 1H), 4.7 (m, 1H), 4.2 (d(br), 1H), 3.9 (d, 1H), 3.7 (d, 1H), 3.5 (m, 2H), 2.3 (t(br), 1H), 1.8 (d(br), 1H), 1.2 (d, 3H).

Workup

  1. temperatureto maintain the homogeneity of the solution
  2. washwashed twice with brine
  3. extractionThe aqueous washes were extracted with another 50 mL of EtOAc
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cbf890c5e157433f9e8702e3fc1ee83e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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