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p-Toluenesulfonic acid monohydrate → N2-((1H-Benzo[d]imidazol-5-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine

HRID 475196
Notes
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Reaction equation

HRID 475196 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]([N:16]([CH3:33])[CH2:17][C:18]4[CH:32]=[CH:31][C:21]5[N:22](C6CCCCO6)[CH:23]=[N:24][C:20]=5[CH:19]=4)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CO.O>[NH:22]1[C:21]2[CH:31]=[CH:32][C:18]([CH2:17][N:16]([CH3:33])[C:12]3[N:11]=[C:10]([NH:9][C:6]4[CH:5]=[C:4]([CH:1]5[CH2:2][CH2:3]5)[NH:8][N:7]=4)[CH:15]=[CH:14][N:13]=3)=[CH:19][C:20]=2[N:24]=[CH:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 86694724N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-((1-(tetrahydro-2H-pyran-2-yl)-1H-benzo[d]imidazol-5-yl)methyl)-pyrimidine-2,4-diamine

Product 1

HCID 178482616N2-((1H-Benzo[d]imidazol-5-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

A tube was charged with a solution of 70 (444 mg, 1.0 mmol) in MeOH (5 mL) and water (1 mL) then TsOH.H2O (190 mg, 1.0 mmol) was added. The tube was sealed and heated at 80° C. overnight. The solvent was evaporated in vacuo and the residue was purified by preparative HPLC to afford 240 mg (66%) of I-12 as a white solid.

Workup

  1. customThe tube was sealed
  2. customThe solvent was evaporated in vacuo
  3. customthe residue was purified by preparative HPLC
  4. customto afford 240 mg (66%) of I-12 as a white solid

Sources & evidence

ORD record
ord-60aa2517997b467bb456641885876271
Source dataset
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08637537B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes