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

HRID 1500807
Notes
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Reaction equation

HRID 1500807 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 143452tert-Butyl piperazine-1-carboxylateHCID 552886216-Methylpyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 86687876tert-Butyl 4-[(4-amino-6-methylpyrrolo[2,1-f][1,2,4]triazin-7-yl)methyl]piperazine-1-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 176Acetic Acid
Solvent

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

  1. customAfter evaporation
  2. washwashed with sat. aq. sodium hydrogencarbonate solution
  3. extractionThe aqueous layer was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes