Tetrahydrofuran → 2-[4-(4-Fluorophenoxy)phenyl]pyrimidine-4-carboxamide

HRID 984058노트

반응식

HRID 984058 반응식
FC1C=CC(OC2C=C[C:10]([C:13]3[N:18]=C(C)C=CN=3)=[CH:9][CH:8]=2)=CC=1.CC(C)([O-:25])C.[K+].C1COCC1.C(O)(=O)C.[F:37][C:38]1[CH:53]=[CH:52][C:41]([O:42][C:43]2[CH:51]=[CH:50][C:46]([C:47]([NH2:49])=[NH:48])=[CH:45][CH:44]=2)=[CH:40][CH:39]=1.COC(OC)CC(=O)C>CN(C=O)C>[F:37][C:38]1[CH:39]=[CH:40][C:41]([O:42][C:43]2[CH:51]=[CH:50][C:46]([C:47]3[N:49]=[C:10]([C:13]([NH2:18])=[O:25])[CH:9]=[CH:8][N:48]=3)=[CH:45][CH:44]=2)=[CH:52][CH:53]=1

참가 물질

7

반응물 5

HCID 8028TetrahydrofuranHCID 2285484,4-Dimethoxy-2-butanoneHCID 99655052-[4-(4-Fluorophenoxy)phenyl]-4-methylpyrimidineHCID 23665647Potassium tert-butoxideHCID 685220074-(4-Fluorophenoxy)benzamidine acetate

생성물 1

HCID 98362702-[4-(4-Fluorophenoxy)phenyl]pyrimidine-4-carboxamide

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

2-[4-(4-Fluorophenoxy)phenyl]-4-methylpyrimidine: A 1M solution of potassium tert-butoxide in THF (11 mL, 11 mmol) was added via syringe to a solution of 4-(4-fluorophenoxy)benzamidine acetate (2.92 g, 10.2 mmol) in DMF. The resulting mixture was heated at 100° C. for 2 hours. Acetylacetaldehyde dimethyl acetal (2 mL, 13.6 mmol) was added via syringe. The reaction was maintained between 100°-110° C. overnight when TLC indicated complete reaction. The reaction was allowed to cool to room temperature and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with water (3 times), dried over MgSO4, filtered, and evaporated under reduced pressure to give the desired product as a yellow oil. 1H NMR (CDCl3): δ8.60 (d, J=5.1, 1H), 8.40 (d, J=9.0, 2H), 7.05-7.00 (m, 7H), 2.57 (s, 3H). This material was carried on without further purification.

후처리

  1. temperatureThe reaction was maintained between 100°-110° C. overnight when TLC
  2. customreaction
  3. temperatureto cool to room temperature
  4. custompartitioned between water and EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washthe combined organic layers were washed with water (3 times)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-8d720f4f29784f4684d127496d26e028
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06867210B2

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