Sodium Bicarbonate → HCID 53251803, compound

HRID 515970Notes

Reaction equation

HRID 515970 reaction equation
[C:1]([C:3]1[C:8]([C:9](OC)=[O:10])=[C:7]([NH:13][C:14]2[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=2)[N:6]=[C:5]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:4]=1)#[N:2].C([O-])(O)=O.[Na+]>[Pd].CO.Cl>[CH:22]1([NH:21][C:5]2[N:6]=[C:7]([NH:13][C:14]3[CH:15]=[C:16]([CH3:20])[CH:17]=[CH:18][CH:19]=3)[C:8]3[C:9](=[O:10])[NH:2][CH2:1][C:3]=3[N:4]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 58317571HCID 58317571, compound

Product 1

HCID 53251803HCID 53251803, compoundYield 69.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of methyl 4-cyano-2-(cyclohexylamino)-6-(m-tolylamino)pyrimidine-5-carboxylate (112.6 mg, 0.308 mmol) and palladium on carbon (26.4 mg, 0.248 mmol) in MeOH (2 mL) and HCl (1N, 2 mL) was stirred at RT for 4 h under a hydrogen atmosphere. Saturated aq NaHCO3 was added and the mixture was stirred for 12 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was extracted with EtOAc. The organic layers were washed with aq NaHCO3, water, and brine, were dried over anhydrous Na2SO4, and then filtered through SiO2. The filtrate was concentrated under reduced pressure and the residue was purified by column chromatography (SiO2, EtOAc) to give a white solid (72.2 mg, 69%). The white solid was recrystallized from EtOH gave the title compound (35.2 mg). 1H NMR (500 MHz, DMSO-d6) δ ppm 1.14-1.17 (m, 1H), 1.24-1.34 (m, 4H), 1.62-1.63 (m, 1H), 1.73-1.78 (m, 2H), 1.89-1.97 (m, 2H), 2.33 (s, 3H), 3.74-3.83 (m, 1H), 4.12-4.17 (m, 2H), 6.86-6.88 (m, 1H), 7.20-7.23 (m, 1H), 7.42-7.52 (m, 2H), 7.76 (s, 1H), 8.00-8.05 (m, 1H), 8.53-8.57 (m, 1H). [M+H] calc'd for C19H24N5O, 338; found, 338.

Workup

  1. stirringthe mixture was stirred for 12 h
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionThe residue was extracted with EtOAc
  5. washThe organic layers were washed with aq NaHCO3, water, and brine
  6. dry with materialwere dried over anhydrous Na2SO4
  7. filtrationfiltered through SiO2
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe residue was purified by column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-da8929c1df58440eb7287f1fa944743a
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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