Triethylamine → 5-(benzyloxymethyl)-8-sec-butyl-6,7-dihydro-8H-pyrolo[3,2-e]pyrazolo[1,5-a]pyrimidine

HRID 1106541Notes

Reaction equation

HRID 1106541 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[C:15]([CH2:16][CH2:17]Cl)=[C:14](Cl)[N:13]2[N:20]=[CH:21][CH:22]=[C:12]2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]([NH2:27])([CH2:25][CH3:26])[CH3:24].C(N(CC)CC)C>CN(C)C=O>[CH2:1]([O:8][CH2:9][C:10]1[C:15]2[CH2:16][CH2:17][N:27]([CH:23]([CH2:25][CH3:26])[CH3:24])[C:14]=2[N:13]2[N:20]=[CH:21][CH:22]=[C:12]2[N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24874Sec-Butylamine2×HCID 187890955-Benzyloxymethyl-7-chloro-6-(2-chloroethyl)pyrazolo[1,5-a]pyrimidine

Product 1

HCID 187891235-(benzyloxymethyl)-8-sec-butyl-6,7-dihydro-8H-pyrolo[3,2-e]pyrazolo[1,5-a]pyrimidineYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 5.0 ml of dimethylformamide were dissolved 0.44 g of 5-(benzyloxymethyl)-7-chloro-6-(2-chloroethyl)pyrazolo-[1,5-a]pyrimidine. To the solution, were added 0.15 g of sec-butylamine and 0.26 ml of triethylamine. The mixture was stirred for 1 hour at room temperature and then for 3 hours in an oil bath heated to 100-110° C. Additional 0.06 g of sec-butylamine were added, and the resultant mixture was stirred for 6.3 hours at the same temperature. After the solvent was distilled off under reduced pressure, and 1N hydrochloric acid was added to the resudue, the mixture was extracted with chloroform. After the chloroform layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resultant crude product was subjected to column chromatography on silica gel (elution solvent: hexane:ethyl acetate=3:1) to obtain 0.33 g (yield: 75.0%) of the intended product.

Workup

  1. temperaturefor 3 hours in an oil bath heated to 100-110° C
  2. distillationAfter the solvent was distilled off under reduced pressure, and 1N hydrochloric acid
  3. additionwas added to the resudue
  4. extractionthe mixture was extracted with chloroform
  5. washAfter the chloroform layer was washed with a saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-36e916d410424d90806029f187ce3e2b
Source dataset
uspto-grants-2000_05
Patent number
US06057330

Reaction notes

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