Sodium → 2-Methylthio-4-isopropylamino-5-nitro-6-allyloxypyrimidine

HRID 597472Notes

Reaction equation

HRID 597472 reaction equation
[CH2:1]([O-:4])[CH:2]=[CH2:3].[Na+].[Na].[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])[C:12]([N+:19]([O-:21])=[O:20])=[C:11](Cl)[N:10]=1>C(O)C=C>[CH3:7][S:8][C:9]1[N:14]=[C:13]([NH:15][CH:16]([CH3:18])[CH3:17])[C:12]([N+:19]([O-:21])=[O:20])=[C:11]([O:4][CH2:1][CH:2]=[CH2:3])[N:10]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 214451032-Methylthio-4-isopropylamino-5-nitro-6-chloro-pyrimidineHCID 23669913Sodium prop-2-enolate

Product 1

HCID 214450702-Methylthio-4-isopropylamino-5-nitro-6-allyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 7858Allyl AlcoholSolvent

Conditions

Temperature
20 °C

Procedure

A solution of sodium allyl alcoholate (prepared from 1.2 g (50 m-moles of sodium in 50 ml of allyl alcohol) is added to 13.2 g (50 m-moles) of 2-methylthio-4-isopropylamino-5-nitro-6-chloro-pyrimidine and the mixture is stirred overnight at 20° C. The allyl alcohol is evaporated off, the residue is suspended in water and extracted with ether. The ethereal extracts are dried over MgSO4 and concentrated to yield 15 g of 2-methylthio-4-isopropylamino-5-nitro-6-allyloxypyrimidine of m.p. 51°-54° C.

Workup

  1. customThe allyl alcohol is evaporated off
  2. extractionextracted with ether
  3. dry with materialThe ethereal extracts are dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0439755111a24939a6721c56e289006e
Source dataset
uspto-grants-1977_03
Patent number
US04014677

Reaction notes

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