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Trifluoroacetic acid → N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine

HRID 1482723
ノート
印刷プレビュー

反応式

HRID 1482723 の反応式
[F:1][C:2]1[C:3]([NH:20][C:21]2[CH:22]=[C:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]=[CH:25][CH:26]=2)=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(O)(C(F)(F)F)=O.CCCCCCC.CCOC(C)=O>C(Cl)Cl>[NH2:27][C:23]1[CH:22]=[C:21]([NH:20][C:3]2[C:2]([F:1])=[CH:7][N:6]=[C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][O:18][CH3:19])=[CH:11][CH:10]=3)[N:4]=2)[CH:26]=[CH:25][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 21899848Ethylacetate heptaneHCID 59174353Tert-butyl (3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate

生成物 1

HCID 59174534N4-(3-aminophenyl)-5-fluoro-N2-(4-(2-methoxyethoxy)phenyl)pyrimidine-2,4-diamine収率 71.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of tert-butyl (3-((5-fluoro-2-((4-(2-methoxyethoxy)phenyl)amino)pyrimidin-4-yl)amino)phenyl)carbamate (550 mg, 1.17 mmol) in DCM (20 mL) was added TFA (2 mL). Stirred for 30 min at rt for 4 h; removed solvent via rotary evaporation and partitioned oil with cold (0° C.) saturated sodium bicarbonate (10 mL) and EtOAc (10 mL), agitated and separated layers. Organic phase was dried over sodium sulfate and the solvent was removed via rotary evaporation to give a dark oil. Flash chromatography using 20%-100% Heptane/EtOAc gradient using combiflash system gave 309 mg of a light pink solid. LC/MS (RT=2.78/(M+1)) 370.2.

後処理

  1. customremoved solvent via rotary evaporation
  2. custompartitioned oil with cold (0° C.) saturated sodium bicarbonate (10 mL) and EtOAc (10 mL)
  3. stirringagitated
  4. customseparated layers
  5. dry with materialOrganic phase was dried over sodium sulfate
  6. customthe solvent was removed via rotary evaporation
  7. customto give a dark oil

出典と根拠

ORDレコード
ord-877ac81f336347e8b76da0c2adf57591
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09415049B2

反応ノート

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