Hydrazine → HCID 178503464, compound

HRID 230197Notes

Reaction equation

HRID 230197 reaction equation
[CH:1]1([C:6]([C:8]2[C:9](Cl)=[N:10][C:11]([S:15][CH3:16])=[N:12][C:13]=2[Cl:14])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)C(C)C)(C)C.[NH2:27][NH2:28]>C1COCC1>[Cl:14][C:13]1[N:12]=[C:11]([S:15][CH3:16])[N:10]=[C:9]2[NH:27][N:28]=[C:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]=12

Participants

5

Reactant 3

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 59812953HCID 59812953, compound

Product 1

HCID 178503464HCID 178503464, compoundYield 119.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopentyl-(4,6-dichloro-2-methylsulfanyl-pyrimidin-5-yl)-methanone (2.0 g, 6.868 mmol) was dissolved in 25 mL dry THF and stirred at 0° C. under nitrogen. N,N-diisopropylethylamine (2.392 mL, 13.763 mmol) was added dropwise, and the reaction mixture was stirred for five minutes. Hydrazine (0.205 mL, 6.525 mmol) was added dropwise, and the reaction was stirred for 16 hours, during which time the reaction mixture was allowed to warm to room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic phase was separated, washed with water, washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to give 2.09 g of 4-Chloro-3-cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine. Mass Spec. M+H=270.

Workup

  1. stirringthe reaction mixture was stirred for five minutes
  2. stirringthe reaction was stirred for 16 hours, during which time the reaction mixture
  3. temperatureto warm to room temperature
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. customthe organic phase was separated
  6. washwashed with water
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b92b7a2ce02a412ba6cfed7069fd998e
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

Loading…