2-Methyltetrahydrofuran → Tert-butyl (5-cyano-4-methylpyrimidin-2-yl)carbamate
Reaction equation
[C:1](/[C:4](=[CH:7]/N(C)C)/[C:5]#[N:6])(=O)[CH3:2].[C:11]([O:15][C:16]([NH:18][C:19]([NH2:21])=[NH:20])=[O:17])([CH3:14])([CH3:13])[CH3:12].CC1CCCO1>>[C:11]([O:15][C:16](=[O:17])[NH:18][C:19]1[N:21]=[C:1]([CH3:2])[C:4]([C:5]#[N:6])=[CH:7][N:20]=1)([CH3:14])([CH3:12])[CH3:13]Participants
Procedure
A 250 ml 3-neck flask was equipped with an overhead stirrer, thermocouple, reflux condenser and heating mantle. The flask was charged with (E)-2-acetyl-3-dimethylamino-acrylonitrile (8.93 g, 63.34 mmol), N-tert-butyloxycarbonyl-guanidine (10 g, 61.56 mmol) and 2-methyltetrahydrofuran (98.76 g). The resultant suspension was stirred and heated to reflux, whereupon the solids were observed to dissolve. The resultant mixture was stirred for about 6 hours, then concentrated by rotary evaporation to yield a solid which was triturated with water (120.00 g) to complete precipitation of the desired product. The resultant suspension was stirred for ˜30 minutes at ambient temperature, then filtered and the wet solid washed twice with water (120.00 g) and dried in a vacuum oven at 75-80° C. under a N2 bleed overnight to yield the title compound.
Workup
- customA 250 ml 3-neck flask was equipped with an overhead stirrer
- temperaturethermocouple, reflux condenser
- temperatureheating mantle
- temperatureheated
- temperatureto reflux, whereupon the solids
- dissolutionto dissolve
- concentrationconcentrated by rotary evaporation
- customto yield a solid which
- customwas triturated with water (120.00 g)
- customprecipitation of the desired product
- filtrationfiltered
- washthe wet solid washed twice with water (120.00 g)
- customdried in a vacuum oven at 75-80° C. under a N2
- waitbleed overnight
Sources & evidence
- ORD record
- ord-431cd86481c24768aa964aa70f76f2af
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359327B2
Reaction notes
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