Isopropylamine → 2-Chloro-4-isopropylamino-thieno[3,4-d]pyrimidine

HRID 1579421Notes

Reaction equation

HRID 1579421 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1.[CH:12]([NH2:15])([CH3:14])[CH3:13]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:15][CH:12]([CH3:14])[CH3:13])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 127128342,4-Dichlorothieno(3,4-d)pyrimidine

Product 1

HCID 215684292-Chloro-4-isopropylamino-thieno[3,4-d]pyrimidineYield 97.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

45 g (0.22 moles) of 2,4-dichloro-thieno[3,4-d]pyrimidine are suspended in 1800 ml of absolute ethyl alcohol. To the cooled mixture 28.5 g (0.48 moles) of isopropylamine are added drop by drop whilst agitating vigorously and maintaining the temperature at between 0° and 5°C. A clear solution is obtained which is agitated for a further hour at ambient temperature. The solution is concentrated, making sure that the temperature of the bath does not exceed 30°C. The syrupy residue is poured into iced water whilst agitating well. A yellow solid is formed which is drained off, washed with water and dried. 49 g of 2-chloro-4-isopropylamino-thieno[3,4-d]pyrimidine are obtained with a yield reaching 98% of theory. M.P. : 189°-191°C.

Workup

  1. temperaturemaintaining the temperature at between 0° and 5°C
  2. customA clear solution is obtained which
  3. stirringis agitated for a further hour at ambient temperature
  4. concentrationThe solution is concentrated
  5. customdoes not exceed 30°C
  6. additionThe syrupy residue is poured into iced water whilst
  7. stirringagitating well
  8. customA yellow solid is formed which
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-1c946295db374fcaa726f3f7acc05141
Source dataset
uspto-grants-1976_01
Patent number
US03931204

Reaction notes

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