Water → HCID 13307163, compound

HRID 1903301Notes

Reaction equation

HRID 1903301 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]=[O:19])[CH2:14][CH2:13]2)[C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.O.[CH3:21][NH2:22]>CO.C(O)C>[CH3:21][NH:22][C:2]1[N:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]=[O:19])[CH2:14][CH2:13]2)[C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 13307210HCID 13307210, compound

Product 1

HCID 13307163HCID 13307163, compound

Reagents, catalysts & solvents 1

HCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

7 g of 2-chloro-4-(N-formylpiperazino)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine was dissolved in 100 ml of a mixture of methanol-ethanol (1:1 by volume), and 50 ml of a 40% aqueous solution of methylamine was added thereto, followed by gently stirring while warming for 7 hours. A large amount of water was added to the mixture which was then extracted with chloroform. The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off and PG,16 the resulting residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane, 1:1 by volume) to obtain 3 g of 2-methylamino-4-(N-formylpiperazino)-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine as colorless prisms having a melting point of 149°-151° C.

Workup

  1. additionwas added
  2. temperaturewhile warming for 7 hours
  3. extractionwas then extracted with chloroform
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customPG,16 the resulting residue was purified by silica gel column chromatography (eluted with ethyl acetate-n-hexane, 1:1 by volume)

Sources & evidence

ORD record
ord-1188d04484dc463c89af1a5b5eabfe0b
Source dataset
uspto-grants-1984_03
Patent number
US04435566

Reaction notes

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