Triethylamine → HCID 131710133, compound

HRID 1604948Notes

Reaction equation

HRID 1604948 reaction equation
C[CH:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([N+:11]([O-:13])=[O:12])=[C:4]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:3]1S.[CH3:21][O-:22].[Na+].C(N(CC)CC)C>CO>[CH3:21][O:22][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[C:5]([N+:11]([O-:13])=[O:12])=[C:4]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10942334Sodium MethoxideHCID 178463440HCID 178463440, compound

Product 1

HCID 131710133HCID 131710133, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

30 g (0.1 mol) of 2-methyl-mercapto-4-ethylamino-5-nitro-6-(3-pentyl-amino)-pyrimidine are dissolved in 400 ml of methanol. A solution of 8.1 g (0.15 mol) of sodium methylate in 100 ml of methanol is added together with 20 ml of triethylamine to the previously prepared solution. The mixture is refluxed for 16 hours, evaporated, and the residue is treated with 200 ml of water. After extracting 3 times with ether, the extracts are dried over MgSO4 , dried, filtered, and the ethereal solution is evaporated, to leave as residue 21.1 g of 2-methyoxy-4-ethylamino-5-nitro-6-(3-pentylamino)-pyrimidine with a boiling point of 162°C/0.001 Torr (74.5 % of theory).

Workup

  1. temperatureThe mixture is refluxed for 16 hours
  2. customevaporated
  3. additionthe residue is treated with 200 ml of water
  4. extractionAfter extracting 3 times with ether
  5. dry with materialthe extracts are dried over MgSO4
  6. customdried
  7. filtrationfiltered
  8. customthe ethereal solution is evaporated

Sources & evidence

ORD record
ord-d9cacc3e8d154cc786a00fe496a049c1
Source dataset
uspto-grants-1976_04
Patent number
US03948914

Reaction notes

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