Hydrochloric Acid → HCID 178424912, compound

HRID 80850Notes

Reaction equation

HRID 80850 reaction equation
C(O)C.[CH3:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:36])[C:12]=2[C:14]2[N:15]=[C:16]([O:34]C)[C:17]3[CH2:23][N:22]([C:24]4[CH:29]=[C:28]([CH:30]([CH3:32])[CH3:31])[CH:27]=[CH:26][C:25]=4[CH3:33])[CH2:21][CH2:20][C:18]=3[N:19]=2)[NH:7][N:6]=1.Cl>ClCCl.C(=O)(O)[O-].[Na+]>[CH3:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:36])[C:12]=2[C:14]2[N:15]=[C:16]([OH:34])[C:17]3[CH2:23][N:22]([C:24]4[CH:29]=[C:28]([CH:30]([CH3:31])[CH3:32])[CH:27]=[CH:26][C:25]=4[CH3:33])[CH2:21][CH2:20][C:18]=3[N:19]=2)[NH:7][N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 178494025HCID 178494025, compound

Product 1

HCID 178424912HCID 178424912, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
85 °C

Procedure

Ethanol (12 mL) was added to 2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (2.07 g, 3.47 mmol), followed by 12 N aqueous hydrochloric acid (12 mL). The mixture was then heated at 85° C. for 18 h. The mixture was cooled to room temperature, diluted with dichloromethane and slowly neutralized with saturated aqueous sodium bicarbonate. The resulting layers were separated and the aqueous layers were extracted with dichloromethane. The organic layers were combined. The combined organics were dried and concentrated. The residue was purified by FCC (0-100% EtOAc/heptane) to provide 2-(3,5-dimethyl-1H-indazol-4-yl)-6-(5-isopropyl-2-methylphenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol. MS (ESI+) m/z 428.3 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe resulting layers were separated
  3. extractionthe aqueous layers were extracted with dichloromethane
  4. customThe combined organics were dried
  5. concentrationconcentrated
  6. customThe residue was purified by FCC (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-b83c4c63276a45bfaf110d4e40abbaaf
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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