N,N-Dimethylaniline → 4-(2-Indanylamino)pyrazolo[3,4-d]pyrimidine

HRID 48405Notes

Reaction equation

O[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.P(Cl)(Cl)(Cl)=O.CN(C)C1C=CC=CC=1.[NH2:25][CH:26]1[CH2:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:27]1>>[CH2:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:34][CH:26]1[NH:25][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12

Participants

Reactant 4

HCID 949N,N-Dimethylaniline

HCID 24813Phosphorus oxychloride

HCID 763102-Aminoindane

HCID 178518059HCID 178518059, compound

Product 1

HCID 227196074-(2-Indanylamino)pyrazolo[3,4-d]pyrimidineYield 56%

Procedure

Using 4-hydroxypyrazolo[3,4-d]pyrimidine (140 mg, 1.0 mmol), phosphorus oxychloride (3.0 ml), and dimethylaniline (0.39 ml, 3.1 mmol), and then 2-aminoindan (400 mg, 3.0 mmol), a similar procedure to Production Example 194 was carried out. The product obtained was purified by silica gel chromatography (hexane:ethyl acetate=5:2) to obtain the title compound (150 mg, 0.56 mmol) having the following physical properties:

Workup

customThe product obtained
customwas purified by silica gel chromatography (hexane:ethyl acetate=5:2)

Sources & evidence

ORD record: ord-9ec3f21238fc484cad2f012e66be07aa
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703421B1

Reaction notes

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