p-Toluenesulfonic acid monohydrate → N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 475177Notes

Reaction equation

HRID 475177 reaction equation
[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH:16]CC4C=CC5N(C6CCCCO6)C=NC=5C=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO.O>[CH:1]1([C:4]2[NH:8][N:7]=[C:6]([NH:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]([NH2:16])[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 71272519N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)pyrimidine-2,4-diamine

Product 1

HCID 86689872N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 32 (406 mg, 0.94 mmol) in MeOH (5 mL) and water (1 mL) was added p-TsOH.H2O (178 mg, 0.94 mmol). The reaction mixture was heated at reflux for 18 h. The solvent was evaporated under reduced pressure and the residue was purified by preparative HPLC to afford 180 mg (55%) of N2-41H-benzo[d]imidazol-5-yl)-methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine (I-13) as white solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9e0624724cf84d34ba34efeac43952fb
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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