Sodium ethoxide → 2-Ethoxy-4-isopropylamino-thieno[3,4-d]pyrimidine

HRID 1579428Notes

Reaction equation

HRID 1579428 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1.[CH3:15][CH2:16][O-:17].[Na+]>C(O)C>[CH2:16]([O:17][C:2]1[N:3]=[C:4]([NH:11][CH:12]([CH3:14])[CH3:13])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1)[CH3:15]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 215684292-Chloro-4-isopropylamino-thieno[3,4-d]pyrimidine

Product 1

HCID 215684412-Ethoxy-4-isopropylamino-thieno[3,4-d]pyrimidineYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4.5 g (0.02 mole) of 2-chloro-4-isopropylamino-thieno[3,4-d]pyrimidine and 0.02 mole sodium ethylate in 200 ml absolute ethyl alcohol is heated in an autoclave at 120°C. for 6 hours. It is then evaporated to dryness. The residue is taken up in a mixture of ether and water; the ether phase is washed with water till neutral pH, dried over Na2SO4, filtered and the solvent is driven off in vacuo. The remaining solid (4.4 g) is recrystallized from a mixture of ethyl acetate-hexane containing 30% ethyl acetate. 3.2 g (68% of theory) of 2-ethoxy-4-isopropylamino-thieno[3,4-d]pyrimidine are obtained. M.P. 155°-156°C.

Workup

  1. customIt is then evaporated to dryness
  2. additionThe residue is taken up in a mixture of ether and water
  3. washthe ether phase is washed with water till neutral pH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customThe remaining solid (4.4 g) is recrystallized from a mixture of ethyl acetate-hexane containing 30% ethyl acetate

Sources & evidence

ORD record
ord-59af96d19bec4fbebc73795401d07572
Source dataset
uspto-grants-1976_01
Patent number
US03931204

Reaction notes

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