Dimethylamine → 1-(dimethylamino)-4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butan-2-ol

HRID 2357986Notes

Reaction equation

HRID 2357986 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[C:18]2[C:13](=[N:14][C:15]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][CH:17]=2)[N:12]([CH2:26][CH2:27][CH:28]2[CH2:30][O:29]2)[N:11]=1.C1COCC1.[CH3:36][NH:37][CH3:38]>C(O)C>[CH3:36][N:37]([CH3:38])[CH2:30][CH:28]([OH:29])[CH2:27][CH2:26][N:12]1[C:13]2=[N:14][C:15]([NH:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][CH:17]=[C:18]2[C:10]([NH:9][C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=2[CH3:8])=[N:11]1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 58836882N3-(2,6-dimethylphenyl)-1-(2-(oxiran-2-yl)ethyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine

Product 1

HCID 160488981-(dimethylamino)-4-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 60 mg (0.15 mmol) of N3-(2,6-dimethylphenyl)-1-(2-(oxiran-2-yl)ethyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine 42 (Example 9, Step A) in 4 mL of absolute ethanol was treated with 375 μl (2.0 M, 0.8 mmol) of a THF solution of dimethylamine. The resulting yellow solution was stirred at room temperature for 2.5 h and then heated to 40° C. for an additional 2 h. The reaction mixture was concentrated and the residue was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 19:1 grading to CH2Cl2:MeOH, 9:1) to give the title compound 43. 1H-NMR (CD3OD) δ 1.75-1.84 (m, 1H), 1.95-2.05 (m, 1H), 2.19 (s, 6H), 2.26 (s, 6H), 2.27-2.43 (m, 2H), 3.63-3.70 (m, 1H), 4.17-4.31 (m, 2H), 7.00 (t, J=7.4 Hz, 1H), 7.09-7.16 (m, 3H), 7.30 (t, J=8.0 Hz, 2H), 7.75 (dd, J=8.7 Hz, 1.0 Hz, 2H), 8.10 (s, 1H). Mass Spectrum (ESI) m/e=446.2 (M+1).

Workup

  1. temperatureheated to 40° C. for an additional 2 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 19:1 grading to CH2Cl2:MeOH, 9:1)

Sources & evidence

ORD record
ord-c8116587ff3d4d2baa5e0e8799494743
Source dataset
uspto-grants-2010_07
Patent number
US07763624B2

Reaction notes

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