Water → HCID 21517680, compound

HRID 1283468Notes

Reaction equation

HRID 1283468 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([O:10][CH3:11])[N:5]=[C:4]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)[N:3]=1.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.O>C(O)C>[C:8]([C:7]1[C:2]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[N:3][C:4]([N:12]2[CH2:17][CH2:16][S:15][CH2:14][CH2:13]2)=[N:5][C:6]=1[O:10][CH3:11])#[N:9]

Participants

5

Reactant 3

HCID 962WaterHCID 4837PiperazineHCID 21517873HCID 21517873, compound

Product 1

HCID 21517680HCID 21517680, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

18 gm (0.067 mol) of 4-chloro-5-cyano-6-methoxy-2-thiomorpholino-pyrimidine (m.p. 218°-219°C) were admixed with 60.3 gm (0.7 mol) of piperazine, and the mixture was heated at 130°C for 3 hours. After cooling, water was added, and the aqueous mixture was extracted with chloroform. The chloroform phase was dried, and the chloroform was removed in vacuo. The residue, the free base reaction product, was dissolved in hot ethanol, and the hydrochloride was precipitated by addition of ethanolic hydrochloric acid, suction-filtered off and washed with ethanol. Yield: 13 gm (54.8% of theory); m.p. 261°C.

Workup

  1. temperatureAfter cooling
  2. extractionthe aqueous mixture was extracted with chloroform
  3. dry with materialThe chloroform phase was dried
  4. customthe chloroform was removed in vacuo
  5. customThe residue, the free base reaction product
  6. customthe hydrochloride was precipitated by addition of ethanolic hydrochloric acid
  7. filtrationsuction-filtered off
  8. washwashed with ethanol

Sources & evidence

ORD record
ord-67e831774ac4418491bbc86d1076eed5
Source dataset
uspto-grants-1976_08
Patent number
US03975384

Reaction notes

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