Hydrochloric Acid → 2-[2-(2,5-Difluoro-phenyl)-ethoxymethyl]-3h-pteridin-4-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][CH2:12][C:13]([NH:15][C:16]([C:18]1[C:23](Cl)=[N:22][CH:21]=[CH:20][N:19]=1)=[O:17])=[NH:14].CC([O-])(C)C.[K+].O.Cl>CS(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][CH2:12][C:13]1[NH:15][C:16](=[O:17])[C:18]2[C:23](=[N:22][CH:21]=[CH:20][N:19]=2)[N:14]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 45 °C
Procedure
Crude 3-chloro-pyrazine-2-carboxylic acid{2-[2-(2,5-difluoro-phenyl)-ethoxy]-1-imino-ethyl}-amide (190 mg) was dissolved in DMSO (1 ml). KOtBu (60 mg, 0.536 mmol) was added and the mixture was heated to 45° C. for 2.5 h. Then water was added, the pH was adjusted to 6 by addition of 0.1 N HCl and the resulting mixture was extracted three times with CH2Cl2. The combined extracts were washed with water (three times) and brine, dried (Na2SO4) and evaporated. The resulting orange brown solid was triturated with Et2O. The remaining solid was filtered off, washed with a small amount of Et2O and dried to give the title compound as a light brown solid (40 mg, 23%). MS: m/e=319.1 [M+H+].
Workup
- extractionthe resulting mixture was extracted three times with CH2Cl2
- washThe combined extracts were washed with water (three times) and brine
- dry with materialdried (Na2SO4)
- customevaporated
- customThe resulting orange brown solid was triturated with Et2O
- filtrationThe remaining solid was filtered off
- washwashed with a small amount of Et2O
- customdried
Sources & evidence
- ORD record
- ord-584e3ea35b454490b2709371762c82dd
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928106B2
Reaction notes
Loading…