Cyclohexane → HCID 57636113, compound

HRID 216106Notes

Reaction equation

HRID 216106 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:4]=1.[BH4-].[Na+].CCOC(C)=O.C1CCCCC1>CO.C1COCC1>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[N:4]=1

Participants

7

Reactant 4

HCID 8078CyclohexaneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 11501553HCID 11501553, compound

Product 1

HCID 57636113HCID 57636113, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophene-2-carbaldehyde [200 mg, 0.54 mmol, Example 8(b)] in MeOH (5 mL) and THF (5 mL) at 0° C. is treated with sodium borohydride (41 mg, 1.08 mmol). The mixture is stirred at ambient temperature for 1 hour and concentrated by rotary evaporator to remove the solvent. The residual solid is dissolved in water and the solution is extracted with ethyl acetate. The organic extract is dried over magnesium sulfate, filtered and concentrated to afford a solid which is subjected to flash column chromatography on silica gel eluting with a mixture of EtOAc and cyclohexane) to afford (5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophen-2-yl)-methanol [75 mg, 37%, Example 9(a)] as a solid. LCMS: RT=6.09 minutes; MS: 372 (M+H). IC50=0.55 nM

Workup

  1. concentrationconcentrated by rotary evaporator
  2. customto remove the solvent
  3. dissolutionThe residual solid is dissolved in water
  4. extractionthe solution is extracted with ethyl acetate
  5. extractionThe organic extract
  6. dry with materialis dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a solid which

Sources & evidence

ORD record
ord-c0a8a1c4591542e082afd0c3e0858a09
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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