Ethanol → 4-Isopropylamino-thieno[3,4-d]pyrimidine

HRID 1579423Notes

Reaction equation

HRID 1579423 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.C(O)C>[Zn].C(O)(=O)C>[CH:12]([NH:11][C:4]1[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=[CH:2][N:3]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 702EthanolHCID 215684292-Chloro-4-isopropylamino-thieno[3,4-d]pyrimidine

Product 1

HCID 215684844-Isopropylamino-thieno[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

15 g of zinc powder are introduced into a solution of 3.9 g (0.017 moles) of 2-chloro-4-isopropylamino-thieno[3,4-d]pyrimidine in 150 ml. of absolute ethyl alcohol. 25 ml. of glacial acetic acid are then added drop by drop wilst agitating. When the addition is completed, the agitation is continued for a further 36 hours at ordinary temperature. The reaction mixture is filtered over hyflocel and the filtrate is poured into 700 ml. of iced water. The pH of the solution is adjusted to 8 with sodium hydroxide and it is extracted several times with ether. The ether phase is washed with water to pH 7, it is dried over sodium sulfate and it is then evaporated to dryness. 1.9 g of 4-isopropylamino-thieno[3,4-d]pyrimidine, still containing a little of the initial product, are obtained. After chromatographic separation and recrystallization from ethyl acetate, one obtains 0.8 g (25% of theory) of the purified product which melts at 230°C with decomposition.

Workup

  1. additionWhen the addition
  2. filtrationThe reaction mixture is filtered over hyflocel
  3. additionthe filtrate is poured into 700 ml
  4. extractionis extracted several times with ether
  5. washThe ether phase is washed with water to pH 7, it
  6. dry with materialis dried over sodium sulfate and it
  7. customis then evaporated to dryness
  8. addition1.9 g of 4-isopropylamino-thieno[3,4-d]pyrimidine, still containing a little of the initial product
  9. customare obtained
  10. customAfter chromatographic separation and recrystallization from ethyl acetate, one
  11. customobtains 0.8 g (25% of theory) of the purified product which melts at 230°C with decomposition

Sources & evidence

ORD record
ord-cb745a29903c45eda9fa9f7e09321420
Source dataset
uspto-grants-1976_01
Patent number
US03931204

Reaction notes

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