Sodium Carbonate → HCID 135948969、化合物

HRID 1170923ノート

反応式

HRID 1170923 の反応式
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

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 59553904HCID 59553904、化合物

生成物 1

HCID 135948969HCID 135948969、化合物

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-25bc6ce3d5d7419088922ac496bf1f6d
出典データセット
uspto-grants-2010_11
特許番号
US07829572B2

反応ノート

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