Bromocyclopentane → 1-Cyclopentyl-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 432158Notes

Reaction equation

HRID 432158 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[NH:16][N:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>CC(N(C)C)=O>[NH2:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]2[N:16]([CH:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[N:15]=[C:14]([C:11]3[CH:12]=[CH:13][C:8]([O:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:9][CH:10]=3)[C:22]=12

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 24758Sodium hydrideHCID 178508717HCID 178508717, compound2×

Product 1

HCID 223471101-Cyclopentyl-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine (Compound 15) (0.91 g) in 50 mL dry dimethylacetamide was stirred under nitrogen at 25° C. while adding 60% sodium hydride (0.20 g). After stirring for 30 minutes bromocyclopentane (0.8 mL) was added and the mixture stirred overnight. After evaporation in vacuo the residue was treated with water and extracted into ethyl acetate. Flash chromatography (3:2 cyclohexane:ethyl acetate) eluted 0.36 g of 1-cyclopentyl-4-(cyclopentylamino)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine as colourless oil. 1H n.m.r. (DMSO) 8.319 (s, 1H), 7.65-7.69(m,2H), 7.40-7.48(m,2H), 7.09-7.23(m,5H), 5.926/5.955(d,1H), 5.17-5.29(quin, 1H), 4.44-4.52(m,1H), 1.86-2.12(m,8H),1.39-1.72(m,8H).

Workup

  1. additionwas added
  2. customAfter evaporation in vacuo the residue
  3. additionwas treated with water
  4. extractionextracted into ethyl acetate
  5. washFlash chromatography (3:2 cyclohexane:ethyl acetate) eluted 0.36 g of 1-cyclopentyl-4-(cyclopentylamino)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidine as colourless oil

Sources & evidence

ORD record
ord-9af6dbe9de364785a7a53048885cb683
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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