Water → HCID 53652465, compound

HRID 597470Notes

Reaction equation

HRID 597470 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1.[CH3:20][SH:21].[Na].O>CCOCC.CS(C)=O>[CH3:20][S:21][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([N+:14]([O-:16])=[O:15])=[C:4]([CH:17]([CH3:19])[CH3:18])[N:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 45051789Methylmercaptan sodiumHCID 54438131HCID 54438131, compound

Product 1

HCID 53652465HCID 53652465, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 14.4 g (50 m-moles) of 2-chloro-4-(3-pentylamino)-5-nitro-6-isopropyl-pyrimidine in 50 ml of ether is added dropwise to a suspension of 3.5 g (50 m-moles) of sodium methylmercaptan in 50 ml of dimethyl sulphoxide. The reaction mixture is stirred for 1 hour at 20° C, then poured into 0.5 liter of water and extracted with ether. The ethereal extracts are dried over MgSO4, dried and evaporated to yield 14 g of 2-methylthio-4-(3-pentylamino)-5-nitro-6-isopropyl-pyrimidine as an oil (nD20 : 1.5757).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ethereal extracts are dried over MgSO4
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-371984034ea7445fb998f8360746fb65
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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