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Ethyl Acetate → 2-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamine

HRID 2053084
ノート
印刷プレビュー

反応式

HRID 2053084 の反応式
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[F:11][C:12]([F:23])([F:22])[C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:10][S:9][C:4]1[N:3]=[C:2]([NH2:1])[CH:7]=[C:6]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([C:12]([F:23])([F:22])[F:11])[CH:18]=2)[N:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 27343883-(Trifluoromethyl)phenylboronic acid

生成物 1

HCID 585132282-Methylsulfanyl-6-(3-trifluoromethylphenyl)-pyrimidin-4-ylamine収率 60.7%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

実験手順

To a stirred solution of 4-amino-6-chloro-2-methylthiopyrimidine (3.5 g) in toluene (45 mL) under a nitrogen atmosphere was added, sequentially, 3-(trifluoromethyl)phenylboronic acid (4.15 g), potassium carbonate (25 mL, 2M) and tetrakis(triphenylphosphine)palladium(0) (1.16 g). The mixture was heated to reflux for ten hours. Ethyl acetate (150 mL) was added and the mixture washed with water (2×100 mL). Organic layer was separated, washed with saturated sodium chloride (100 mL), dried over sodium sulphate and solvent was evaporated under reduced pressure to yield crude product. Purification by flash chromatography yielded product 2-methylsulfanyl-6-(3-trifluoromethyl-phenyl)-pyrimidin-4-ylamine (3.45 g)

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for ten hours
  3. washthe mixture washed with water (2×100 mL)
  4. customOrganic layer was separated
  5. washwashed with saturated sodium chloride (100 mL)
  6. dry with materialdried over sodium sulphate and solvent
  7. customwas evaporated under reduced pressure
  8. customto yield crude product
  9. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-a34b067471a64c818b8713335d50002e
出典データセット
uspto-grants-2008_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07326715B2

反応ノート

読み込み中…

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