Sodium Carbonate → HCID 135948969, 화합물

HRID 1170923노트

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HRID 1170923 반응식
Cl[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27]C)=[N:7][C:6]=2[CH:5]=[CH:4][N:3]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[OH:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:8]1[N:9]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:10](=[O:12])[C:11]2[C:2]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[N:3][CH:4]=[CH:5][C:6]=2[N:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59553904HCID 59553904, 화합물

생성물 1

HCID 135948969HCID 135948969, 화합물

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

5-Chloro-2-(2-methoxy-phenyl)-3-phenethyl-3H-pyrido[4,3-d]pyrimidin-4-one, phenylboronic acid (1.1 equiv.), palladium tetrakis(triphenylphosphine) (7 mol %) and 2N aqueous Na2CO3 (4 equiv.) were combined in dioxane (0.5 mL) and heated in a microwave for 15 minutes to 140° C. The reaction mixture was cooled to room temperature, diluted with water and extracted (3×) with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous MgSO4 and filtered. The crude products were purified on preparative TLC using 1:1 ethyl acetate:hexane. The desired product can be obtained by using the methyl ether deprotection conditions employing BCl3 and isolation conditions found in the final step of Example 1. 1H NMR (400 MHz, CDCl3) δ 8.90 (s, 1H), 8.78 (d, 1H), 7.53 (m, 2H), 7.46 (m, 3H), 7.37 (t, 1H), 7.29 (d, 1H), 7.13 (m, 3H), 6.97 (m, 2H), 6.77 (m, 2H), 4.30 (t, 2H), 2.79 (t, 2H). MS m/z 420.4 (M+H)+.

후처리

  1. temperatureheated in a microwave for 15 minutes to 140° C
  2. extractionextracted (3×) with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe crude products were purified on preparative TLC

출처 및 근거

ORD 기록
ord-25bc6ce3d5d7419088922ac496bf1f6d
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829572B2

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