Ethanol → 5-(4-Formylphenyl)pyrimidine

HRID 50560

反応式

HRID 50560 の反応式
C([O-])([O-])=O.[Na+].[Na+].C(O)C.Cl.Cl[C:12]1[CH:13]=[N:14][CH:15]=[N:16][CH:17]=1.[CH:18]([C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1)=[O:19]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[N:14]1[CH:13]=[C:12]([C:23]2[CH:24]=[CH:25][C:20]([CH:18]=[O:19])=[CH:21][CH:22]=2)[CH:17]=[N:16][CH:15]=1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 227351705-Chloropyrimidine hydrochloride

生成物 1

HCID 38612125-(4-Formylphenyl)pyrimidine収率 48.7%

試薬・触媒・溶媒 3

HCID 10974057(Butane-1,4-diyl)bis(diphenylphosphane)--dichloropalladium (1/1)触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1 M aq. Na2CO3 (20 mL) and ethanol (10 mL) were added to a solution of 5-chloropyrimidine hydrochloride (3.03 g, 20.06 mmol, prepared as described in WO 9821188), 4-formylphenylboronic acid (3.90 g, 26.01 mmol) and [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.60 g, 0.99 mmol) in toluene (40 mL) and the mixture was heated to reflux for 18 h. The cooled reaction mixture was diluted with ethyl acetate, washed with sat. aq. NaHCO3 and brine, dried (MgSO4), and concentrated. Purification by chromatography (SiO2, 4:1 hexane/ethyl acetate) yielded 1.80 g (42%) of the title compound. MS 185 (M+H)+.

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe cooled reaction mixture
  4. washwashed with sat. aq. NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by chromatography (SiO2, 4:1 hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-ae4430c86d0f46dba2137ba2e4b21c4e
出典データセット
uspto-grants-2004_03
特許番号
US06713455B2

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