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

HRID 1912647노트

반응식

HRID 1912647 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ac2c0115ee04a3dbd1dc7652f949ebd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609676B2

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