Sodium Hydroxide → 6-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid

HRID 2171791Notes

Reaction equation

HRID 2171791 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][CH:5]([C:8]2[S:22][C:11]3[N:12]=[C:13]([CH3:21])[N:14]=[C:15]([C:16]([O:18]CC)=[O:17])[C:10]=3[CH:9]=2)[CH2:4][CH2:3]1.[OH-].[Na+]>CCO>[CH3:1][C:2]1([CH3:23])[CH2:3][CH2:4][CH:5]([C:8]2[S:22][C:11]3[N:12]=[C:13]([CH3:21])[N:14]=[C:15]([C:16]([OH:18])=[O:17])[C:10]=3[CH:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118024048Ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate

Product 1

HCID 1180240036-(4,4-Dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylate (1.0 g) and EtOH (10 mL) was added a 1 M aqueous NaOH solution (3.9 mL) under ice-cooling, followed by stirring at the same temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid was added thereto, followed by stirring for 30 minutes. The precipitate was collected by filtration, washed with water and then with hexane, dried by flowing air, and then dried under reduced pressure to obtain 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidine-4-carboxylic acid (900 mg).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and 1 M hydrochloric acid
  3. additionwas added
  4. stirringby stirring for 30 minutes
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. dry with materialwith hexane, dried
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-46277893be474a3f94e94c2b89b53ef0
Source dataset
uspto-grants-2015_06
Patent number
US09051339B2

Reaction notes

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