Hydrazine → HCID 178478395, compound

HRID 1192450Notes

Reaction equation

HRID 1192450 reaction equation
[CH:1]1([C:4]([C:6]2[C:7](Cl)=[N:8][CH:9]=[N:10][C:11]=2[Cl:12])=O)[CH2:3][CH2:2]1.[NH2:14][NH2:15]>C1COCC1>[Cl:12][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[NH:14][N:15]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:6]=12

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86053660HCID 86053660, compound

Product 1

HCID 178478395HCID 178478395, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Cyclopropyl-(4,6-dichloro-pyrimidin-5-yl)-methanone (0.75 g, 3.5 mmol), anhydrous hydrazine (0.13 mL, 4.1 mmol) and THF (35 mL) was stirred at room temperature for 4 hours. The reaction was partitioned between water and EtOAc. The organic layer was washed with brine, dried and passed through a short silica gel pad to give 4-Chloro-3-cyclopropyl-1H-pyrazolo[3,4-d]pyrimidine (0.50 g, 74%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 11.87 (s, 1H), 8.80 (s, 1H), 2.55 (m, 1H), 1.15 (m, 2H), 1.14 (m, 2H).

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. washThe organic layer was washed with brine
  3. customdried

Sources & evidence

ORD record
ord-1b316be060cb42d491959da9d5a439c4
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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