2-Methyltetrahydrofuran → Tert-butyl (5-cyano-4-methylpyrimidin-2-yl)carbamate

HRID 1470230ノート

反応式

HRID 1470230 の反応式
[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]

参加物

4

反応物 3

HCID 73012-MethyltetrahydrofuranHCID 299417973-(Dimethylamino)-2-acetylacrylonitrileHCID 178454308HCID 178454308、化合物

生成物 1

HCID 59140971Tert-butyl (5-cyano-4-methylpyrimidin-2-yl)carbamate

実験手順

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.

後処理

  1. customA 250 ml 3-neck flask was equipped with an overhead stirrer
  2. temperaturethermocouple, reflux condenser
  3. temperatureheating mantle
  4. temperatureheated
  5. temperatureto reflux, whereupon the solids
  6. dissolutionto dissolve
  7. concentrationconcentrated by rotary evaporation
  8. customto yield a solid which
  9. customwas triturated with water (120.00 g)
  10. customprecipitation of the desired product
  11. filtrationfiltered
  12. washthe wet solid washed twice with water (120.00 g)
  13. customdried in a vacuum oven at 75-80° C. under a N2
  14. waitbleed overnight

出典と根拠

ORDレコード
ord-a27883248e434802a1ecc6e11eed6ab7
出典データセット
uspto-grants-2015_04
特許番号
US09006432B2

反応ノート

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