N-Iodosuccinimide → 5-(4-Chloro-phenyl)-7-cyclopropyl-3-iodo-pyrazolo[1,5-a]pyrimidine

HRID 2237856Notes

Reaction equation

HRID 2237856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][CH:19]=[C:10]3[N:9]=2)=[CH:4][CH:3]=1.[I:20]N1C(=O)CCC1=O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[N:11]3[N:17]=[CH:18][C:19]([I:20])=[C:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 670009395-(4-Chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670008755-(4-Chloro-phenyl)-7-cyclopropyl-3-iodo-pyrazolo[1,5-a]pyrimidineYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 5-(4-chloro-phenyl)-7-cyclopropyl-pyrazolo[1,5-a]pyrimidine (1.08 g, 4.0 mmol) and N-iodo-succinimide (0.90 g, 4.0 mmol) in N,N-dimethylformamide (8 mL) was stirred at 20° C. for 40 min. The heterogeneous mixture was partitioned between EtOAc and water. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was triturated with diethyl ether to give 5-(4-chloro-phenyl)-7-cyclopropyl-3-iodo-pyrazolo[1,5-a]pyrimidine (1.45 g, 92%) as a yellow solid. MS (ISP) 395.8 [(M+H)+]; mp 189-190° C.

Workup

  1. customThe heterogeneous mixture was partitioned between EtOAc and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-8fd53a5cf4434306b0b113070e236bfa
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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