Ammonium formate → 6-(4-Methylpiperazin-1-yl)-4-(propan-2-yloxy)pyridin-3-amine

HRID 518830Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[C:11]([N+:18]([O-])=O)=[CH:10][N:9]=2)[CH2:4][CH2:3]1.C([O-])=O.[NH4+]>[Pd].CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[CH:10][C:11]([NH2:18])=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:13]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

In a microwave tube, 390 mg of 1-methyl-4-[5-nitro-4-(propan-2-yloxy)pyridin-2-yl]piperazine are introduced into 12 ml of methanol. 525 mg of ammonium formate and 210 mg of Pd/C (10%) are added. The reaction medium is microwave-heated at 80° C. for 5 minutes. The mixture is filtered on Clarcel and the Clarcel is rinsed with methanol. The filtrate is concentrated under reduced pressure, so as to give 340 mg of 6-(4-methylpiperazin-1-yl)-4-(propan-2-yloxy)pyridin-3-amine in the form of a brown oil.

Workup

filtrationThe mixture is filtered on Clarcel
washthe Clarcel is rinsed with methanol
concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record: ord-f99c49cdc04b4d4fbcc42958b91200db
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115140B2

Reaction notes

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