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Potassium Phosphate, Tribasic → 6-{[6-(4-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester

HRID 1926971
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HRID 1926971 반응식
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 58016901Methyl 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoate

생성물 1

HCID 580169116-{[6-(4-Fluorophenyl)-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester

시약·촉매·용매 2

HCID 11180781
trans-Bis(dicyclohexylamine)palladium(II) acetate
촉매
HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

Add 3 mg (0.01 mmol) trans-bis(dicyclohexylamine)palladium(II) acetate [T. Bin, J. Org. Chem. 2004, 69, 4330-4335] to a mixture of 100 mg (0.22 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester, 47 mg (0.34 mmol) 4-fluorophenylboronic acid and 95 mg (0.45 mmol) potassium phosphate in 5 ml dioxan, and stir for 21 h at 80° C. After filtering off the solid, concentrate the filtrate by vacuum evaporation. Purify the residue by preparative RP-HPLC (gradient: water/acetonitrile). 59 mg (57% of theor.) of the desired product is obtained.

후처리

  1. filtrationAfter filtering off the solid
  2. concentrationconcentrate the filtrate
  3. customby vacuum evaporation
  4. customPurify the residue by preparative RP-HPLC (gradient: water/acetonitrile)

출처 및 근거

ORD 기록
ord-8baca4ed8e8b4f03b58c800a2bb128ca
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183246B2

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