Diisopropylethylamine → HCID 136395934, compound

HRID 618660Notes

Reaction equation

HRID 618660 reaction equation
Cl[C:2]1[N:11]2[C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=[C:10]2[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.C(N(C(C)C)CC)(C)C.[BH4-].[Na+]>[Pd].O>[C:15]1([N:13]2[C:12](=[O:21])[N:11]3[CH2:2][NH:3][C:4]4[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=4[C:10]3=[N:14]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4311764Sodium borohydrideHCID 154288415-Chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one

Product 1

HCID 136395934HCID 136395934, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-chloro-2-phenyl-7,8,9,10-tetrahydro-1,2,4-triazolo[4,3-c]quinazolin-3-one (150 mg, 0.5 mmol), diisopropylethylamine (130 ml, 0.74 mmol) and 10% Pd-C (30 mg) was hydrogenated under H2 balloon for 1 hour. The reaction was filtered through Celite. NaBH4 (30 mg, 0.79 mmol) was added to the filtrate and the mixture was heated to reflux temperature. The reaction was poured into water and extracted with CH2Cl2 (3×50 ml). The combined organic layers were dried over Na2SO4 and evaporated under reduced pressure. The residue was triturated with ethanol and filtered to afford 2-phenyl-5,6,7,8,9,10-hexahydro-1,2,4-triazolo[4,3-c]-quinazolin-3-one (Compound 31), m.p. 158-159° C.

Workup

  1. customfor 1 hour
  2. filtrationThe reaction was filtered through Celite
  3. temperaturethe mixture was heated
  4. temperatureto reflux temperature
  5. extractionextracted with CH2Cl2 (3×50 ml)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ethanol
  9. filtrationfiltered

Sources & evidence

ORD record
ord-8178ab0e9f064ca595b2414481396fcf
Source dataset
uspto-grants-1999_09
Patent number
US05955465

Reaction notes

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