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

HRID 575795
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인쇄 미리보기

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HRID 575795 반응식
[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
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참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 8028Tetrahydrofuran용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-38ab35ee37874f6c8ae4616c0af7e4ae
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09034900B2

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