Diisopropylethylamine → n-{3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]propyl}-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 496894Notes

Reaction equation

HRID 496894 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH2:17])[CH2:10][CH2:9]1.Cl[C:23]1[N:28]=[CH:27][N:26]=[C:25]2[N:29]([CH3:32])[N:30]=[CH:31][C:24]=12.C(N(C(C)C)CC)(C)C>CN1CCCC1=O.C(OCC)(=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[Cl:21])[O:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:23]2[N:28]=[CH:27][N:26]=[C:25]3[N:29]([CH3:32])[N:30]=[CH:31][C:24]=23)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2197514-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidineHCID 1317237633-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]propylamine, dihydrochloride salt

Product 1

HCID 22322345n-{3-[4-(3,4-Dichlorophenoxy)-1-piperidinyl]propyl}-1-methyl-1h-pyrazolo[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The product from step (ii) (0.08 g), 4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (0.054 g) and diisopropylethylamine (0.082 g) in 1-methyl-2-pyrrolidinone (2 ml) was heated at 50° C. for 3 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was dried and the solvent removed under reduced pressure. Purification was by chromatography eluting with 9% methanol/dichloromethane. Yield 0.052 g

Workup

  1. washwashed with water
  2. customThe organic layer was dried
  3. customthe solvent removed under reduced pressure
  4. customPurification
  5. washeluting with 9% methanol/dichloromethane

Sources & evidence

ORD record
ord-da3d0a9abbc5437f81bf56be176d9f07
Source dataset
uspto-grants-2005_09
Patent number
US06946478B2

Reaction notes

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