Ammonia → 5-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-

HRID 384725

반응식

HRID 384725 반응식
[NH3:1].[Cl:2][C:3]1[C:8]([CH:9]=[O:10])=[C:7](Cl)[N:6]=[CH:5][N:4]=1>C1(C)C=CC=CC=1.O>[NH2:1][C:7]1[C:8]([CH:9]=[O:10])=[C:3]([Cl:2])[N:4]=[CH:5][N:6]=1

참가 물질

5

반응물 2

HCID 222Ammonia3회HCID 8196914,6-Dichloro-5-pyrimidinecarbaldehyde

생성물 1

HCID 842305-Pyrimidinecarboxaldehyde, 4-amino-6-chloro-

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
60 °C

실험 절차

NH3 (g) was blown through a solution of 4,6-dichloro-pyrimidine-5-carbaldehyde Compound 1a (50 g, 282.5 mmol) in toluene (565 mL, 0.5M) for 3 mins using a 12C glass frit, then the mixture was warmed at 60° C. with stirring for 30 min. NH3 (g) was blown through the reaction mixture a second time for 3 min and the reaction was heated for 30 mins. NH3 (g) was blown through the reaction mixture a third time for 3 min and the reaction was heated for a final 20 mins. The reaction mixture was diluted with H2O (1 L), and extracted with EtOAc (1×750 mL, 3×500 mL). The organic extracts were washed with brine (4×) and dried (Na2SO4), then concentrated to afford 4-amino-6-chloro-pyrimidine-5-carbaldehyde Compound 1b (38.5 g, 87%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 10.27 (s, 1H), 8.74 (br s, 1H), 8.58 (br s, 1H), 8.42 (s, 1H).

후처리

  1. customfor 3 min
  2. temperaturethe reaction was heated for 30 mins
  3. customfor 3 min
  4. temperaturethe reaction was heated for a final 20 mins
  5. extractionextracted with EtOAc (1×750 mL, 3×500 mL)
  6. washThe organic extracts were washed with brine (4×)
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4bedd63239c14ec7bc7dc051ac5b440a
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367825B2

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