Sodium Carbonate → 5-(3'-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

HRID 2416295ノート

反応式

HRID 2416295 の反応式
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:20][CH2:21][CH3:22])[C:18]=1I)[CH2:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)[CH3:2].[NH2:23][C:24]1[CH:25]=[C:26]([B])[CH:27]=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C>[NH2:23][C:24]1[CH:29]=[C:28]([C:18]2[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([CH2:7][C:8]3[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=3)=[CH:16][C:17]=2[O:20][CH2:21][CH3:22])[CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 201616813-Aminophenyl-boronHCID 226369195-(3,5-Diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine

生成物 1

HCID 98646205-(3'-Amino-2,6-diethoxy-biphenyl-4-ylmethyl)-pyrimidine-2,4-diamine

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

Tetrakis-triphenylphosphine-palladium (555 mg; 0.48 mmol) is suspended in dimethoxyethane (7 ml) while gassing with argon, and 5-(3,5-diethoxy-4-iodo-benzyl)-pyrimidine-2,4-diamine (example 1) (4.14 g; 10 mmol) in dimethoxyethane (60 ml) is added. After stirring for 15 minutes at room temperature, 3-amino-phenylboron acid monnohydrate (2.37 g; 15 mmol) in ethanol (17 ml) is added, the mixture is stirred at room temperature for a further 10 minutes, aqueous 2 M sodium carbonate solution (44 ml) is added and the mixture is then boiled under reflux for 4 hours. The reaction mixture is concentrated and the residue is stirred with water and filtered off with suction. The filter cake is stirred with MeOH (230 ml) and filtered off with suction. The filtrate is concentrated and the residue is chromatographed over silica gel (225 g) with methylene chloride/methanol/ammonia (19/1/0.05, later 90/10/1). The pure fractions are combined and concentrated and the residue is dried under a high vacuum.

後処理

  1. additionis added
  2. stirringthe mixture is stirred at room temperature for a further 10 minutes
  3. temperatureunder reflux for 4 hours
  4. concentrationThe reaction mixture is concentrated
  5. stirringthe residue is stirred with water
  6. filtrationfiltered off with suction
  7. stirringThe filter cake is stirred with MeOH (230 ml)
  8. filtrationfiltered off with suction
  9. concentrationThe filtrate is concentrated
  10. customthe residue is chromatographed over silica gel (225 g) with methylene chloride/methanol/ammonia (19/1/0.05, later 90/10/1)
  11. concentrationconcentrated
  12. customthe residue is dried under a high vacuum

出典と根拠

ORDレコード
ord-2d825a8584b74715bba1d95c02d8d6fe
出典データセット
uspto-grants-2004_11
特許番号
US06821980B1

反応ノート

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