Methanol → 7-bromo-3,4-dihydropyrazino[2,3-b]pyrazin-2(1H)-one trifluoroacetate
Reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH:15]CC2C=CC(OC)=CC=2OC)[C:5]([NH:8][CH2:9][C:10](OCC)=[O:11])=[N:6][CH:7]=1.CO.[C:29]([OH:35])([C:31]([F:34])([F:33])[F:32])=[O:30]>>[F:32][C:31]([F:34])([F:33])[C:29]([OH:35])=[O:30].[Br:1][C:2]1[N:3]=[C:4]2[NH:15][C:10](=[O:11])[CH2:9][NH:8][C:5]2=[N:6][CH:7]=1Participants
4
Conditions
- Temperature
- 75 °C
Procedure
Ethyl 2-(5-bromo-3-(2,4-dimethoxybenzylamino)pyrazin-2-ylamino)acetate (0.484 g, 1.138 mmol), methanol (0.461 mL, 11.38 mmol) and TFA (7 mL) were combined in a sealable vessel with a stirbar. The system was purged with nitrogen. The resulting mixture was sealed, stirred vigorously and heated at 75° C. in an oil bath for 25 min. The resulting mixture was diluted with water (14 mL) and stirred at room temperature for 5 min. Solids were collected by vacuum filtration, washed with water and diethyl ether and dried under high vacuum to give the desired product (0.375 g, 1.093 mmol, 96% yield) as a pink solid. MS (ESI) m/z 229.0 [M]+, 231.3 [M+2]+.
Workup
- customThe system was purged with nitrogen
- customThe resulting mixture was sealed
- additionThe resulting mixture was diluted with water (14 mL)
- stirringstirred at room temperature for 5 min
- filtrationSolids were collected by vacuum filtration
- washwashed with water and diethyl ether
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-646fc263d2f546808a98d9787b05fe94
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193692B2
Reaction notes
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