Potassium Hydroxide → N2-((1H-Indol-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 475186Notes

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]=[CH:21][N:22]5S(C4C=CC(C)=CC=4)(=O)=O)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[K+]>CO>[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]=[CH:21]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 50 (330 mg, 0.73 mmol) in MeOH (5.0 mL) was added a solution of KOH (2.0 N, 5 mL). The mixture was heated in a sealed tube at 100° C. overnight then concentrated in vacuo. The residue was purified by preparative HPLC to afford 145 mg (57%) of I-38 as white solid.

Workup

concentrationthen concentrated in vacuo
customThe residue was purified by preparative HPLC
customto afford 145 mg (57%) of I-38 as white solid

Sources & evidence

ORD record: ord-0c280b1616fb4ba48871e09ac9c00b61
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637537B2

Reaction notes

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