Dimethylformamide → HCID 20361819, compound

HRID 1679685Notes

Reaction equation

HRID 1679685 reaction equation
[OH:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[N:5]=[CH:4][C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].[CH2:22](I)[CH3:23].CN(C)C=O>CN(P(N(C)C)(N(C)C)=O)C>[CH2:22]([N:5]1[CH:4]=[C:3]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2](=[O:1])[N:7]2[N:8]=[CH:9][N:10]=[C:6]12)[CH3:23]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 178469693HCID 178469693, compound

Product 1

HCID 20361819HCID 20361819, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Ethyl 7-hydroxy-1,2,4-triazolo [1,5-a]pyrimidine-6-carboxylate (10.4g, 50mM), potassium carbonate (7.0g, 50mM), ethyl iodide (8.0ml, 15mM), dry dimethylformamide (80ml) and hexamethylphosphorotriamide (80ml) was heated at 80° C for 4 hours. The resulting mixture was evaporated in vacuo and water added (100ml). The solution was washed with ether (5 × 100ml) then extracted with ethyl acetate (10 × 100ml). The ethyl acetate extracts were dried over magnesium sulphate, filtered and evaporated in vacuo. The crystals were filtered off and recrystallised from ethyl acetate. 37.9% yield (4.47g); mpt 129° - 131° C. δ (CDCl3) 8.62 (1H,s) and 8.12 (1H,s), ##STR55## 4.47 (2H,q) and 4.38 (2H,q), (OCH2CH3 and NCH2CH3), 1.62 (3H,t) and 1.50 (3H,t), (OCH2CH3 and NCH2CH3); ν max (KBr) 3400 (broad) 1715, 1690, 1610, 1570, 1480, 1370, 1325, 1210, 1175, 790cm-1 ; λmax (EtOH) 209 (εm 12,400), 252 (εm 8,260) and 290 (εm 11,800)nm.

Workup

  1. customThe resulting mixture was evaporated in vacuo and water
  2. additionadded (100ml)
  3. washThe solution was washed with ether (5 × 100ml)
  4. extractionthen extracted with ethyl acetate (10 × 100ml)
  5. dry with materialThe ethyl acetate extracts were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. filtrationThe crystals were filtered off
  9. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3869001213ba49bea5330394bf7eaad6
Source dataset
uspto-grants-1978_03
Patent number
US04081545

Reaction notes

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