Triethylamine → HCID 136169452, compound

HRID 1707976Notes

Reaction equation

HRID 1707976 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([O:11]COCCOC)=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([C:22]([NH:24][NH2:25])=[O:23])[N:6]=1)([CH3:4])[CH3:3].[C:26](C1NC=CN=1)(C1NC=CN=1)=[O:27].C(N(CC)CC)C>C1COCC1>[CH3:3][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:18]([CH3:19])([CH3:20])[CH3:21])[N:8]=[C:7]([C:22]2[O:23][C:26](=[O:27])[NH:25][N:24]=2)[N:6]=1)([CH3:4])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 67780415HCID 67780415, compound

Product 1

HCID 136169452HCID 136169452, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy) methoxy]-2-pyrimidine carboxylic acid hydrazide (1.0 g, 2.8 mmoles), carbonyl diimidazole (0.7 g, 4.2 mmoles), and triethylamine (0.6 g, 5.9 mmoles) are combined in 20 mL of THF and the reaction mixture is stirred at room temperature under argon for 64 hours. The reaction is quenched with 50 mL of 10% HOAc/H2O. The organics are extracted into ether (3×30 mL) and washed with 50 nil of brine. The solvent is evaporated and the residue is taken up in 20 mL of acetic acid. The reaction mixture is warmed to reflux for 18 hours. It is cooled to room temperature and diluted with 150 mL of H2O. The organics are extracted into EtOAc (3×100 mL) and washed with H2O (3×100 mL) followed by brine (3×100 mL). The solvent is evaporated, and the remaining oil is purified by flash chromatography (50% EtOAc|Hexane). Yield of 5-[4,6-bis (1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]-1,3,4-oxadiazole-2 (3H)-one=0.11 g (13%), mp 230°-232° C.

Workup

  1. customThe reaction is quenched with 50 mL of 10% HOAc/H2O
  2. extractionThe organics are extracted into ether (3×30 mL)
  3. washwashed with 50 nil of brine
  4. customThe solvent is evaporated
  5. temperatureThe reaction mixture is warmed
  6. temperatureto reflux for 18 hours
  7. temperatureIt is cooled to room temperature
  8. additiondiluted with 150 mL of H2O
  9. extractionThe organics are extracted into EtOAc (3×100 mL)
  10. washwashed with H2O (3×100 mL)
  11. customThe solvent is evaporated
  12. customthe remaining oil is purified by flash chromatography (50% EtOAc|Hexane)

Sources & evidence

ORD record
ord-fcd23ac0ad454fc8a2fc7cfd10b5e23b
Source dataset
uspto-grants-1994_10
Patent number
US05356898

Reaction notes

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