Potassium Carbonate → 4-Chloro-5-(2,2-diethoxyethyl)-6-phenylpyrimidine

HRID 717578노트

반응식

HRID 717578 반응식
Cl[C:2]1[C:7]([CH2:8][CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:6]([Cl:16])[N:5]=[CH:4][N:3]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O>[Cl:16][C:6]1[C:7]([CH2:8][CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:3]=[CH:4][N:5]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 197943054,6-Dichloro-5-(2,2-diethoxyethyl)pyrimidine

생성물 1

HCID 898151274-Chloro-5-(2,2-diethoxyethyl)-6-phenylpyrimidine수율 63.6%

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

The 4,6-dichloro-5-(2,2-diethoxyethyl)pyrimidine (1.1 g), phenyl boronic acid (500 mg) and potassium carbonate (556 mg) were dissolved in toluene (15 mL) and water (1.5 mL). The reaction mixture was degassed with nitrogen for 30 minute and then Pd(PPh3)4 (230 mg) was added. The reaction mixture was again degassed with nitrogen for 20 minutes before heated to 100° C. for 3 hours in a sealed tube. The reaction mixture was filtered through a celite pad and washed with ethyl acetate (2×20 mL). The combined filtrate was washed with water (10 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography using EtOAc/hexane (0.5:9.5) as eluent to afford 4-chloro-5-(2,2-diethoxyethyl)-6-phenylpyrimidine (800 mg) as colorless viscous liquid. 1H NMR (DMSO-d6): δ 1.07-1.10 (t, 6H), 3.21-3.23 (d, 2H), 3.32-3.36 (q, 2H), 3.37-4.00 (q, 2H), 4.79-4.81 (t, 1H), 7.47-7.49 (m, 3H), 7.63-7.66 (m, 2H), 8.91 (s, 1H).

후처리

  1. customThe reaction mixture was degassed with nitrogen for 30 minute
  2. additionPd(PPh3)4 (230 mg) was added
  3. customThe reaction mixture was again degassed with nitrogen for 20 minutes
  4. filtrationThe reaction mixture was filtered through a celite pad
  5. washwashed with ethyl acetate (2×20 mL)
  6. washThe combined filtrate was washed with water (10 mL) and brine (10 mL)
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-bf4eb33386f2450d96ff54c391a7dcf5
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193725B2

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