Hydrochloric Acid → HCID 54137330, compound

HRID 2286676Notes

Reaction equation

HRID 2286676 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[CH:16]=[C:15](Cl)[N:14]=[C:13]([C:18](=[N:24][O:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:12]=1.Cl>CN(C)C=O.O>[NH2:10][C:11]1[CH:16]=[C:15]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:14]=[C:13]([C:18](=[N:24][O:25][CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 54233444HCID 54233444, compound

Product 1

HCID 54137330HCID 54137330, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of thiophenol (2.55 g) in N,N-dimethylformamide (20 ml) was added 50% sodium hydride (1.1 g) under cooling in an ice bath and the mixture was stirred for 20 minutes at 0° C. to 5° C. To the mixture was added ethyl 2-(4-amino-6-chloropyrimidin-2-yl)-2-methoxyiminoacetate (2.0 g) and the mixture was stirred for 6 hours at ambient temperature. The resultant mixture was poured into cold water, adjusted to pH7 with diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue was subjected to column chromatography on silica gel (50 g) using a mixture of chloroform and ethyl acetate (3:1 by valume) as an eluent. The fractions containing the object product were collected and evaporated to give ethyl 2-(4-amino-6-phenylthiopyrimidin-2-yl)-2-methoxyiminoacetate (syn isomer) (460 mg), mp 154°-156° C.

Workup

  1. temperatureunder cooling in an ice bath
  2. stirringthe mixture was stirred for 6 hours at ambient temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated to dryness
  7. additiona mixture of chloroform and ethyl acetate (3:1 by valume) as an eluent
  8. additionThe fractions containing the object product
  9. customwere collected
  10. customevaporated

Sources & evidence

ORD record
ord-97f83a4267a6424d87ce7166ecdab333
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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