Formaldehyde → tert-Butyl 4-[(4-amino-6-methylpyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]piperazine-1-carboxylate

HRID 1500807Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH2:11].[CH2:12]=O.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(O)(=O)C>[NH2:11][C:5]1[C:4]2=[CH:3][C:2]([CH3:1])=[C:10]([CH2:12][N:17]3[CH2:18][CH2:19][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:16]3)[N:9]2[N:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 6-methylpyrrolo[2,1-f][1,2,4]triazin-4-amine (500 mg, 3.3 mmol; preparation described in PCT Int. Pat. Appl. WO 2007/056170) in acetic acid (8 ml) was treated with 37% aq. formaldehyde solution (328 μl, 4.04 mmol) and tert-butyl piperazine-1-carboxylate (754 mg, 4.04 mmol). The mixture was stirred at 60° C. overnight. After evaporation, the residue was taken up in ethyl acetate and washed with sat. aq. sodium hydrogencarbonate solution. The aqueous layer was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and evaporated affording 1.2 g of the crude product which was used in the next step without further purification.

Workup

customAfter evaporation
washwashed with sat. aq. sodium hydrogencarbonate solution
extractionThe aqueous layer was extracted twice with ethyl acetate
dry with materialThe combined organic phases were dried over magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-4a30e75a1d6c4eeaafd74b6a7c99a20c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206184B2

Reaction notes

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