Potassium Phosphate, Tribasic → HCID 178488539、化合物

HRID 2169221ノート

反応式

HRID 2169221 の反応式
[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2Br)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:1]([O:5][C:6]([C:8]1[C:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:12]([OH:22])[N:11]=[C:10]([CH2:23][C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 178488296tert-butyl 2-[(2-bromo-5-methoxyphenyl)methyl]-4-oxo-5-phenylmethoxy-1H-pyrimidine-6-carboxylate

生成物 1

HCID 178488539HCID 178488539、化合物収率 56.94%

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 22253497Water butanol溶媒

実験手順

To a stirred solution of 5-benzyloxy-2-(2-bromo-5-methoxybenzyl)-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (138) (3 g, 5.988 mmol) in n-butanol:water (3:1, 12 mL) were added phenyl boronic acid (1.096 g, 8.982 mmol), X-Phos (427 mg, 0.898 mmol), K3PO4 (4.44 g, 20.958 mmol) and Pd(dba)2 (275 mg, 0.479 mmol). The reaction mixture was refluxed for 10 h. After completion of the reaction, the mixture was evaporated to get a crude product which was purified by a normal silica column using 2% methanol in dichloromethane to afford 5-benzyloxy-6-hydroxy-2-(4-methoxybiphenyl-2-ylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (139) (1.7 g, 56.94%) as an off-white solid.

後処理

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customAfter completion of the reaction
  3. customthe mixture was evaporated
  4. customto get a crude product which
  5. customwas purified by a normal silica column

出典と根拠

ORDレコード
ord-84d8c9c281ee4dbeaf5be15e439850ea
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

読み込み中…