Hydrazine hydrate (1:1) → HCID 20094178, compound

HRID 273782Notes

Reaction equation

HRID 273782 reaction equation
Cl[C:2]1[C:3]2[S:12][CH:11]=[CH:10][C:4]=2[N:5]=[C:6]([CH2:8][Cl:9])[N:7]=1.O.[NH2:14][NH2:15]>O1CCCC1>[Cl:9][CH2:8][C:6]1[N:7]=[C:2]([NH:14][NH2:15])[C:3]2[S:12][CH:11]=[CH:10][C:4]=2[N:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 200941424-Chloro-2-(chloromethyl)thieno[3,2-d]pyrimidine

Product 1

HCID 20094178HCID 20094178, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

3. 8.2 g of 4-chloro-2-(chloromethyl)thieno[3,2-d]pyrimidine are dissolved in 500 ml of absolute tetrahydrofuran. The solution is cooled to 5° C. 7 ml of hydrazine hydrate are added dropwise within 5 min., whereby a solution results and the temperature rises to 15° to 20° C. The reaction mixture is stirred at room temperature for 15 h. and then evaporated in a vacuum. The residue is stirred with 100 ml of saturated aqueous sodium hydrogen carbonate solution for 30 min. and then filtered off. The crystals are washed neutral with water and dried in a vacuum. 14.7 g of 2-(chloromethyl)-4-hydrazinothieno[3,2-d]-pyrimidine are obtained. A further 1.0 g of 2-(chloromethyl)-4-hydrazinothieno[3,2-d]pyrimidine are obtained by extracting the filtrate with chloroform.

Workup

  1. customwhereby a solution results
  2. customrises to 15° to 20° C
  3. customevaporated in a vacuum
  4. stirringThe residue is stirred with 100 ml of saturated aqueous sodium hydrogen carbonate solution for 30 min.
  5. filtrationfiltered off
  6. washThe crystals are washed neutral with water
  7. customdried in a vacuum

Sources & evidence

ORD record
ord-911d0d7334fb464b8e4f979a0f0487a8
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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