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Sodium Carbonate → 5-(2,6-Dichloropyrimidin-4-yl)-1,3-dimethylpyridin-2-one

HRID 575795
ノート
印刷プレビュー

反応式

HRID 575795 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH3:10][N:11]1[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[C:13]([CH3:26])[C:12]1=[O:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[N:3]=[C:4]([C:15]2[CH:14]=[C:13]([CH3:26])[C:12](=[O:27])[N:11]([CH3:10])[CH:16]=2)[CH:5]=[C:6]([Cl:8])[N:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 773782,4,6-TrichloropyrimidineHCID 712703091,3-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-dihydropyridin-2-one

生成物 1

HCID 1180221595-(2,6-Dichloropyrimidin-4-yl)-1,3-dimethylpyridin-2-one収率 55.5%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

A mixture of 2,4,6-trichloropyrimidine (275 mg, 1.5 mmol), 1,3-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-one (246 mg, 1 mmol), Pd(OAc)2 (20 mg), triphenylphosphine (16 mg), and 2M Na2CO3 (1 mL, 2 mmol) in THF (6.7 mL) was purged with nitrogen for 5 min, capped, and heated to 80° C. for 3 h. After the mixture was filtered through a short bed of celite, the filtrate was concentrated in vacuo and purified by silica gel column chromatography using a gradient (0 to 100%) EtOAc in DCM to afford the title compound (150 mg, 55%) as a white solid. LCMS (M+H)+=271.

後処理

  1. customwas purged with nitrogen for 5 min
  2. customcapped
  3. filtrationAfter the mixture was filtered through a short bed of celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-38ab35ee37874f6c8ae4616c0af7e4ae
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09034900B2

反応ノート

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