p-Toluenesulfonic acid monohydrate → N2-((1H-Indazol-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 475258Notes

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][CH2:17][C:18]4[CH:26]=[CH:25][CH:24]=[C:23]5[C:19]=4[CH:20]=[N:21][N:22]5C4CCCCO4)[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:23]2[C:19](=[C:18]([CH2:17][NH:16][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:26]=[CH:25][CH:24]=2)[CH:20]=[N:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 200 (215 mg, 0.5 mmol) in MeOH (5 mL) and water (1 mL) was added p-TsOH.H2O (95 mg, 0.5 mmol) and the mixture was heated in a sealed tube at 80° C. overnight. The solvent was evaporated in vacuo. The residue was purified by preparative HPLC to afford 110 mg (63%) of I-59 as white solid.

Workup

customThe solvent was evaporated in vacuo
customThe residue was purified by preparative HPLC
customto afford 110 mg (63%) of I-59 as white solid

Sources & evidence

ORD record: ord-cd6dff43458949af8ec36efd104b05d3
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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