Monobenzone → 4-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine

HRID 491657ノート

反応式

HRID 491657 の反応式
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][C:21]2[CH:22]=[CH:23][N:24]=[C:19]([Cl:18])[N:20]=2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 7638MonobenzoneHCID 24758Sodium hydrideHCID 775312,4-Dichloropyrimidine

生成物 1

HCID 177554044-(4-Benzyloxy-phenoxy)-2-chloro-pyrimidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a stirred RT slurry of NaH (0.5 g of 60% oil dispersion, 12.6 mmol) in 15 mL DMF was added 4-benzyloxyphenol (2.40 g, 12.0 mmol). The mixture was stirred for 10 min before 2,4-dichloropyrimidine (1.79 g, 12.0 mmol) was added. A mild exotherm occurred. The reaction was stirred for 2 h and quenched with saturated aqueous NaHCO3. The reaction was diluted with EtOAc, the layers were separated, and the organic layer was washed twice with 2 N NaOH, once with brine, then dried over Na2SO4. The organic layer was filtered and concentrated in vacuo to yield crude title compound contaminated with minor impurities by H-NMR. MS (MH+)=NA; Calc'd 312.76 for C17H13ClN2O2.

後処理

  1. additionwas added
  2. customquenched with saturated aqueous NaHCO3
  3. additionThe reaction was diluted with EtOAc
  4. customthe layers were separated
  5. washthe organic layer was washed twice with 2 N NaOH, once with brine
  6. dry with materialdried over Na2SO4
  7. filtrationThe organic layer was filtered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-40dac93449dc448c8499b6c401dc640c
出典データセット
uspto-grants-2009_05
特許番号
US07531553B2

反応ノート

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