Sodium ethoxide → 5-Bromo-2-(propan-2-yl)pyrimidine-4-carboxylic acid
Reaction equation
Cl.[C:2]([NH2:7])(=[NH:6])[CH:3]([CH3:5])[CH3:4].CC[O-].[Na+].[C:12]([OH:20])(=[O:19])/[C:13](=[C:15](\[CH:17]=O)/[Br:16])/Br>CCO>[Br:16][C:15]1[C:13]([C:12]([OH:20])=[O:19])=[N:6][C:2]([CH:3]([CH3:5])[CH3:4])=[N:7][CH:17]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred suspension of isobutyramidine hydrochloride (6.47 g, 47.5 mmol) at rt in EtOH (30 ml) under an argon atmosphere was added NaOEt solution (21 ml, 21% in EtOH) over min. The suspension was heated to 50° C. and a solution of mucobromic acid (5.7 g, 22.1 mmol) in EtOH (24 ml) was added dropwise over 5 min at 50° C. An additional portion of NaOEt solution (12 ml, 21% in EtOH) was added dropwise over 5 min. The mixture was then cooled to rt. The solids were filtered off, and the cake was washed with plenty of ethanol. The filtrate was concentrated to leave the crude product as a light brown solid. The crude material was triturated in 2 N HCl (100 ml). The product was collected by filtration, washed with plenty of H2O and plenty of n-heptane and dried to give the product (2.09 g, 73%) as beige solid.
Workup
- temperatureThe mixture was then cooled to rt
- filtrationThe solids were filtered off
- washthe cake was washed with plenty of ethanol
- concentrationThe filtrate was concentrated
- customto leave the crude product as a light brown solid
- customThe crude material was triturated in 2 N HCl (100 ml)
- filtrationThe product was collected by filtration
- washwashed with plenty of H2O and plenty of n-heptane
- customdried
Sources & evidence
- ORD record
- ord-c303b4d526974779bee739452e0e1913
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08703768B2
Reaction notes
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