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

HRID 475191Notes

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[C:26]5[N:25]=[CH:24][N:23](C6CCCCO6)[C:22]=5[CH:21]=[CH:20][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:23]1[C:22]2[CH:21]=[CH:20][CH: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)[C:26]=2[N:25]=[CH:24]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 60 (110 mg, 0.26 mmol) and p-TsOH.H2O (44 mg, 0.26 mmol) in MeOH (5 mL) and water (1 mL) was heated at 80° C. for 14 h. The solvent was removed in vacuo. The crude product was purified by preparative HPLC to afford 45 mg (51%) I-39 as white solid.

Workup

customThe solvent was removed in vacuo
customThe crude product was purified by preparative HPLC
customto afford 45 mg (51%)

Sources & evidence

ORD record: ord-7452a1575c3a4dd9b05983798aa43d8e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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