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

HRID 1523379노트

반응식

HRID 1523379 반응식
[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]

참가 물질

4

반응물 3

HCID 73012-MethyltetrahydrofuranHCID 299417973-(Dimethylamino)-2-acetylacrylonitrileHCID 178454308HCID 178454308, 화합물

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79964761832d4b7cb2b5bf455e576b3e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079884B2

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