Chlorine → 5-chloro-2-cyclopropyl-6-(diethoxymethyl)-1H-pyrimidin-4-one

HRID 907426노트

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HRID 907426 반응식
[Cl:1]Cl.[CH:3]1([C:6]2[NH:7][C:8]([CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])=[CH:9][C:10](=[O:12])[N:11]=2)[CH2:5][CH2:4]1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[Cl:1][C:9]1[C:10](=[O:12])[N:11]=[C:6]([CH:3]2[CH2:4][CH2:5]2)[NH:7][C:8]=1[CH:13]([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19]

참가 물질

5

반응물 3

HCID 24526ChlorineHCID 517045Sodium AcetateHCID 178471100HCID 178471100, 화합물2회

생성물 1

HCID 1784711825-chloro-2-cyclopropyl-6-(diethoxymethyl)-1H-pyrimidin-4-one수율 98%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
29 °C

실험 절차

Chlorine was carefully passed through 2-cyclopropyl-6-(diethoxymethyl)-4(1H)-pyrimidinone (i.e. the product of Example 3) (46.0 g, 0.193 mol) and sodium acetate (18.8 g, 0.229 mol) in acetic acid (185 mL). The temperature was maintained in the range of about 28-30° C. When the starting material had been consumed, the flow of chlorine was stopped immediately. Toluene (185 mL) was added, and the mixture was evaporated under reduced pressure. The process was repeated. The mixture was partitioned between ethyl acetate (450 mL) and water (50 mL). The organic layer was further washed with water (4×50 mL), dried and evaporated to leave the product as an off-white solid (51.75 g, 98% yield). Product recrystallized from hexanes had a melting point of 109-111° C.

후처리

  1. customWhen the starting material had been consumed
  2. additionToluene (185 mL) was added
  3. customthe mixture was evaporated under reduced pressure
  4. customThe mixture was partitioned between ethyl acetate (450 mL) and water (50 mL)
  5. washThe organic layer was further washed with water (4×50 mL)
  6. customdried
  7. customevaporated

출처 및 근거

ORD 기록
ord-5a572ebe93fa40be9367688fd1647dfb
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08013155B2

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