Hydrochloric Acid → HCID 58413244, compound

HRID 532282Notes

Reaction equation

HRID 532282 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([O:13][C:14]1[C:19]([NH:20][C:21]2[C:22]3[C:29]([CH3:30])=[C:28]([C:31]([O:33]C)=[O:32])[S:27][C:23]=3[N:24]=[CH:25][N:26]=2)=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([O:13][C:14]1[C:19]([NH:20][C:21]2[C:22]3[C:29]([CH3:30])=[C:28]([C:31]([OH:33])=[O:32])[S:27][C:23]=3[N:24]=[CH:25][N:26]=2)=[CH:18][CH:17]=[CH:16][N:15]=1)[CH3:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58413402HCID 58413402, compound

Product 1

HCID 58413244HCID 58413244, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-(2-(4-(tert-butoxycarbonylamino)butan-2yloxy)pyridin-3ylamino)-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate (600 mg) was dissolved in methanol (10 ml) and NaOH (1M; 2.5 ml) was added. The reaction mixture was heated at reflux for 15 minutes. Then it was cooled to room temperature and HCl (1M; 2.5 ml) was added. Methanol was evaporated and the residue was dissolved in dichloromethane. The mixture was washed with water, the organic layer was dried and concentrated in vacuo. The residue was triturated with Et2O.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 15 minutes
  3. customMethanol was evaporated
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe mixture was washed with water
  6. customthe organic layer was dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-e10143fed58847968143f095576e3e80
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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