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Trifluoroacetic acid → 5-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzyl]-pyrimidine-2,4-diamine

HRID 38323
ノート
印刷プレビュー

反応式

HRID 38323 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([C:9]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=2[CH:21]([CH3:29])[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(Cl)Cl>[CH3:20][O:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:11]([CH2:9][C:5]2[C:6]([NH2:8])=[N:7][C:2]([NH2:1])=[N:3][CH:4]=2)=[C:12]([CH:21]([CH3:29])[CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:13]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 21226445Aluminium lithium hydrideHCID 59598674(2,4-Diamino-pyrimidin-5-yl)-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-methanone

生成物 1

HCID 16119167
5-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzyl]-pyrimidine-2,4-diamine
収率 58%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2,4-diamino-pyrimidin-5-yl)-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]methanone (0.413 g, 0.4 mmol) in 10 mL THF was added LiAlH4 (0.73 mL, 1.0 M in THF) over 5 min. After gas evolution ceased the mixture was warmed to reflux. After 3 h the mixture was cooled to 0° C. and quenched by the Fieser method. After 30 min the mixture was filtered through a pad of celite and concentrated in vacuo to give a crude white solid. To a solution of this solid in 5 mL CH2Cl2 was added trifluoroacetic acid (1.1 mL, 14.0 mmol) followed by triethylsilane (0.4 mL, 2.8 mmol). After 30 min 50 mL 10% K2CO3 was as added and the mixture was extracted with ethyl acetate and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (95:5 CH2Cl2) afforded 5-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-benzyl]-pyrimidine-2,4-diamine (0.066 g, 58%) as a white foam; melting point (HCl salt) 227.1-227-4° C.

後処理

  1. temperaturewas warmed to reflux
  2. customquenched by the Fieser method
  3. filtrationAfter 30 min the mixture was filtered through a pad of celite
  4. concentrationconcentrated in vacuo
  5. customto give a crude white solid
  6. additionas added
  7. extractionthe mixture was extracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialThe combined organics were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customPurification via flash chromatography (95:5 CH2Cl2)

出典と根拠

ORDレコード
ord-2628ddb7554649dfa566c881b79eec0e
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08524725B2

反応ノート

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