Sodium Hydroxide → N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine

HRID 2409068Notes

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]C(C4C5C=CN(S(C6C=CC(C)=CC=6)(=O)=O)C=5C=CN=4)C)[N:11]=3)[CH:5]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>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

Conditions

Temperature: 80 °C

Procedure

A mixture of (±)—N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-(1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethyl)pyrimidine-2,4-diamine (563 mg, 1.10 mmol) and sodium hydroxide (132 mg, 3.29 mmol) in MeOH (20 mL) and water (50 mL) was stirred at 80° C. for 3 h. The reaction mixture was concentrated in vacuo. The crude product was purified by reverse phase preparative HPLC to afford N2-1-(1H-pyrrolo[3,2-c]pyridin-4-yl)ethyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)pyrimidine-2,4-diamine: MS (ESI) m/z: 361.2 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated in vacuo
customThe crude product was purified by reverse phase preparative HPLC

Sources & evidence

ORD record: ord-3ef8d9d81eb445998aecf5a8da813d65
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815877B2

Reaction notes

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