Ethanethiol → 24DIAMINOPYRIMIDINE53MEO4IPRENYL5ETOBz

HRID 127023Notes

Reaction equation

HRID 127023 reaction equation
[CH2:1](S)[CH3:2].[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]C)[C:18]([C:23]([CH3:25])=[CH2:24])=[C:17]([O:26][CH3:27])[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:16]=[C:17]([O:26][CH3:27])[C:18]([C:23]([CH3:25])=[CH2:24])=[C:19]([O:21][CH2:1][CH3:2])[CH:20]=2)=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24758Sodium hydrideHCID 479082HCID 479082, compound

Product 1

HCID 2327611624DIAMINOPYRIMIDINE53MEO4IPRENYL5ETOBz

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

A solution of 16.1 ml. of ethylmercaptan in 130 ml. of dimethylformamide was added dropwise while stirring and gassing with nitrogen to a suspension of 10.4 g. of sodium hydride (50%) in 130 ml. of dimethylformamide. After the evolution of gas had ceased, the mixture was stirred at room temperature for an additional 15 minutes and treated with a solution of 13 g. of 2,4-diamino-5-(4-isopropenyl-3,5-dimethoxybenzyl)-pyrimidine in 260 ml. of dimethylformamide. The mixture was stirred at 120° C. for 6 hours. The solvent was removed under a high vacuum. The solid residue was dissolved in water, filtered and the filtrate was adjusted to pH 4 with 1-N hydrochloric acid. The acid solution was then adjusted to pH 8 with ammonia and the solid crude product was isolated in a yield of 98%. Recrystallization from methanol yielded pure 2,4-diamino-5-(3-hydroxy-4-isopropenyl-5-methoxybenzyl)-pyrimidine, having a melting point of 218°-219° C.

Workup

  1. additiongassing with nitrogen to a suspension of 10.4 g
  2. stirringthe mixture was stirred at room temperature for an additional 15 minutes
  3. additiontreated with a solution of 13 g
  4. stirringThe mixture was stirred at 120° C. for 6 hours
  5. customThe solvent was removed under a high vacuum
  6. dissolutionThe solid residue was dissolved in water
  7. filtrationfiltered
  8. customthe solid crude product was isolated in a yield of 98%
  9. customRecrystallization from methanol yielded pure 2,4-diamino-5-(3-hydroxy-4-isopropenyl-5-methoxybenzyl)-pyrimidine

Sources & evidence

ORD record
ord-21cb081a210f4b45a87f17cfd03a3cf9
Source dataset
uspto-grants-1981_03
Patent number
US04254286

Reaction notes

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