Iodoethane → 3-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

HRID 1093158Notes

Reaction equation

HRID 1093158 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[CH:10][C:5]2=[C:4]([N:11]2[CH2:17][CH:16]3[O:18][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[N:3]=1.[H-].[Na+].[CH2:21](I)[CH3:22]>CN1CCCC1=O>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:21][CH3:22])[N:9]=[CH:10][C:5]2=[C:4]([N:11]2[CH2:17][CH:16]3[O:18][CH:13]([CH2:14][CH2:15]3)[CH2:12]2)[N:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 201118843-(6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 866293763-(6-chloro-1-ethyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To 6-chloro-4-(8-oxa-3-aza-bicyclo[3.2.1]oct-3-yl)-1H-pyrazolo[3,4-d]pyrimidine (0.418 mmol), NaH (60% in oil, 2.1 mmol) and ethyl iodide (2.1 mmol) is added N-methylpyrrolidinone (1 mL). After 5 min the reaction mixture is heated in the microwave at 175 C for 10 min. Reverse phase HPLC gave the product.

Workup

  1. temperatureAfter 5 min the reaction mixture is heated in the microwave at 175 C for 10 min
  2. customReverse phase HPLC gave the product

Sources & evidence

ORD record
ord-6ef23fb342b042fab6f19587dd712827
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

Loading…