2-Bromopropane → 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 237966Notes

Reaction equation

HRID 237966 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:18](Br)([CH3:20])[CH3:19]>CN(C=O)C>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:18]([CH3:20])[CH3:19])[N:3]=1

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178508725HCID 178508725, compound

Product 1

HCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (2 g, 0.0077 mol) and K2CO3 (4.2 g, 0.031 mol) in DMF (50 ml) was brought to 80° C. under an argon atomosphere. Isopropylbromide (1.0 g, 0.0084 mol) was added with a syringe. Reaction was refluxed under argon atmosphere for 2 hours. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with EtOAc. Organic phases concentrated in vacuo and purified using silica gel column chromatography [MeOH—CH2Cl2, 5:95] yielding BA12 (1.68 g, 72% yield). ESI-MS (M+H)+ m/z calcd 304.0, found 304.1.

Workup

  1. customwas brought to 80° C. under an argon
  2. customReaction
  3. temperaturewas refluxed under argon atmosphere for 2 hours
  4. customSolid K2CO3 was removed by filtration
  5. customSolvent was partially removed in vacuo
  6. additionSodium citrate (50 ml) was added
  7. customreaction
  8. extractionwas extracted with EtOAc
  9. concentrationOrganic phases concentrated in vacuo
  10. custompurified

Sources & evidence

ORD record
ord-f12c3261da8145af9cc8dd36207ceb29
Source dataset
uspto-grants-2014_02
Patent number
US08642604B2

Reaction notes

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