Hydrochloric Acid → HCID 86753117, compound

HRID 2393758Notes

Reaction equation

HRID 2393758 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[CH:6]=[CH:5][N:4]=1.[C:10]([C:13]1[CH:14]=[C:15]([CH:17]=[C:18]([C:20](=[O:22])[CH3:21])[CH:19]=1)[NH2:16])(=[O:12])[CH3:11].Cl.[OH-].[K+]>O>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:16][C:15]2[CH:14]=[C:13]([C:10](=[O:12])[CH3:11])[CH:19]=[C:18]([C:20](=[O:22])[CH3:21])[CH:17]=2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14797Potassium HydroxideHCID 971134-Chloro-2-methylthiopyrimidineHCID 463010Cni H1894

Product 1

HCID 86753117HCID 86753117, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Illustrative compound 62 was synthesized by mixing 803 mg (5 mmol) 2-methylmercapto-4-chloropyrimidine and 886 mg (5 mmol) 3,5-diacetylaniline in 20 ml of water. In addition, 0.42 ml concentrated HCl was added. This reaction mixture was heated at 90°-100° C. for 4 hours, and then cooled down in an ice bath. The cooled mixture had 5 ml of 1N KOH added to neutralize the acid pH from the HCl. The mixture was stirred for 10 minutes in an ice bath to form a precipitate. The precipitate was filtered out to give 1.44 g dry pale brown crude product. A thin layer chromatography (TLC) analysis in methanol:CH2 Cl2 (1:25) showed only one spot. The crude precipitate was recrystalized from methoxyethanol and dried under vacuum to give 1.42 grams of pure 2-methylmercapto-4-(3',5'-diacetylphenyl) aminopyrimidine (compound 62) with an overall yield of 94%. The NMR analysis found the formula C15H15N3O2S with a molecular weight of 301.38.

Workup

  1. customIllustrative compound 62 was synthesized
  2. temperatureThis reaction mixture was heated at 90°-100° C. for 4 hours
  3. temperaturecooled down in an ice bath
  4. additionadded
  5. customto form a precipitate
  6. filtrationThe precipitate was filtered out
  7. customto give 1.44 g
  8. customdry pale brown crude product
  9. customThe crude precipitate was recrystalized from methoxyethanol
  10. customdried under vacuum

Sources & evidence

ORD record
ord-b0b696ef2e0f499e80e48ae550b35ca5
Source dataset
uspto-grants-1998_09
Patent number
US05808068

Reaction notes

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