HCID 3645909, compound → HCID 178435023, compound

HRID 894829Notes

Reaction equation

HRID 894829 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1.[BH4-].[Na+]>C(O)C.C(Cl)(Cl)Cl>[Cl:1][C:2]1[NH:3][CH2:4][C:5]2[C:10]([CH3:11])=[C:9]([CH3:12])[S:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 3645909HCID 3645909, compoundHCID 4311764Sodium borohydride

Product 1

HCID 178435023HCID 178435023, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 21889567Chloroform ethanolSolvent

Procedure

To a solution of 4.66 g of 2,4-dichloro-5,6-dimethylthieno[2,3-d]pyrimidine in 150 ml of ethanol-chloroform (1:1 by volume) was slowly added 2.32 g of sodium borohydride with stirring. The mixture was stirred at room temperature for 6 hours and the solvent removed in vacuo. To the solid residue was added 50 ml of water and the insoluble material was filtered, washed with water, dried, and recrystallized from benzene to give 2.05 g of 2-chloro-5,6-dimethyl-3,4-dihydrothieno[2,3-d]pyrimidine, mp 170°-172° C.

Workup

  1. stirringThe mixture was stirred at room temperature for 6 hours
  2. customthe solvent removed in vacuo
  3. additionTo the solid residue was added 50 ml of water
  4. filtrationthe insoluble material was filtered
  5. washwashed with water
  6. customdried
  7. customrecrystallized from benzene

Sources & evidence

ORD record
ord-4e42bcc474f14d85ae1c31f9f5806486
Source dataset
uspto-grants-1981_08
Patent number
US04284773

Reaction notes

Loading…