Triethylamine → HCID 131710133, compound

HRID 973114Notes

Reaction equation

HRID 973114 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-3d3929286fac480d82cf56019a670476
Source dataset
uspto-grants-1977_10
Patent number
US04055411

Reaction notes

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