Sodium hydride → 4-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile

HRID 1912647ノート

反応式

HRID 1912647 の反応式
[CH2:1]([O:8][C:9]1[C:10](Cl)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][C:26]=1[F:32])#[N:24].[H-].[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([NH:29][C:28]2[CH:30]=[CH:31][C:25]([C:23]#[N:24])=[C:26]([F:32])[CH:27]=2)=[N:11][CH:12]=[N:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27834134-Amino-2-fluorobenzonitrileHCID 866659375-(Benzyloxy)-4-chloro-6-p-tolylpyrimidine

生成物 1

HCID 669583574-(5-(Benzyloxy)-6-p-tolylpyrimidin-4-ylamino)-2-fluorobenzonitrile収率 76.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The compound from step 4 (0.3 g, 0.96 mmol) was dissolved in DMF (4.83 ml), 4-cyano-3-fluoroaniline (0.131 g, 1 eq) and NaH (0.155 g of 60% dispersion in mineral oil, 4 eq) were added. After 1 hour LCMS showed complete conversion, the reaction was quenched with NH4Cl(sat) and extracted with EtOAc. The extracts were dried concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexane) to give 0.3 g of the title compound.

後処理

  1. customconversion, the reaction was quenched with NH4Cl(sat)
  2. extractionextracted with EtOAc
  3. customThe extracts were dried
  4. concentrationconcentrated
  5. customthe residue purified by silica gel chromatography (0-20% EtOAc in hexane)

出典と根拠

ORDレコード
ord-3ac2c0115ee04a3dbd1dc7652f949ebd
出典データセット
uspto-grants-2013_12
特許番号
US08609676B2

反応ノート

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