Ethanethiol → HCID 20348468, compound

HRID 1701124Notes

Reaction equation

HRID 1701124 reaction equation
C(S)C.[H-].[Na+].[NH2:6][C:7]1[N:12]=[C:11]([NH2:13])[C:10]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23]C)[CH:16]=2)=[CH:9][N:8]=1>CN(C)C=O>[NH2:6][C:7]1[N:12]=[C:11]([NH2:13])[C:10]([CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([OH:23])[CH:16]=2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 884962,4-Pyrimidinediamine, 5-((3,5-dimethoxyphenyl)methyl)-

Product 1

HCID 20348468HCID 20348468, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 32.2 g. of ethylmercaptan in 310 ml. of dimethylformamide was added dropwise with cooling and nitrogen gasification to a suspension of 25 g. of 50% sodium hydride in 310 ml. of dimethylformamide. The mixture was subsequently treated with a solution of 27 g. of 2,4-diamino-5-(3,5-dimethoxybenzyl)pyrimidine in 310 ml. of dimethylformamide, stirred at 100° C. for 17 hours, cooled down to room temperature and concentrated under a high vacuum. The residue, dissolved in a small amount of water, was filtered, the filtrate was extracted three times with 50 ml. of benzene each time and the aqueous phase was adjusted to pH 4-5 with concentrated hydrochloric acid while cooling with ice-water. Subsequently, it was brought to pH 9 with concentrated ammonia and the precipitated product, 23.3 g. of α-(2,4-diamino-5-pyrimidyl)-5-methoxy-m-cresol of melting point 254°-255° C. (from methanol) was isolated.

Workup

  1. temperaturewith cooling
  2. additionnitrogen gasification to a suspension of 25 g
  3. additionThe mixture was subsequently treated with a solution of 27 g
  4. concentrationconcentrated under a high vacuum
  5. dissolutionThe residue, dissolved in a small amount of water
  6. filtrationwas filtered
  7. extractionthe filtrate was extracted three times with 50 ml
  8. temperaturewhile cooling with ice-water

Sources & evidence

ORD record
ord-0a43b737426f47568eacdcae421a4ffe
Source dataset
uspto-grants-1980_03
Patent number
US04191758

Reaction notes

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