Sodium Carbonate → HCID 58742226、化合物

HRID 1514440ノート

反応式

HRID 1514440 の反応式
I[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[CH3:10][C:11]1[S:12][C:13](B2OC(C)(C)C(C)(C)O2)=[C:14]([CH3:16])[N:15]=1.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:10][C:11]1[S:12][C:13]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=2)=[C:14]([CH3:16])[N:15]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 38589014-Iodo-2-(methylthio)pyrimidine2 回HCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole

生成物 1

HCID 58742226HCID 58742226、化合物収率 76%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 10311-Propanol溶媒

実験手順

To a solution of 4-iodo-2-methylsulfanyl-pyrimidine (390 mg, 1.56 mmol), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-thiazole (633 mg, 2.65 mmol added portionwise), Na2CO3 (215 mg, 2.02 mmol), triphenylphosphine (42 mg, 0.15 mmol) in nPrOH (25 ml), Pd(OAc)2 (11 mg, 0.047 mmol) was added and the mixture was refluxed for 2 hour. The solvent was evaporated under vacuum, and the crude was dissolved in DCM and washed with water. The organic phase was dried (Na2SO4) and evaporated. A second batch of this compound was prepared according to the same protocol starting from 0.39 mmol of 4-iodo-2-methylsulfanyl-pyrimidine. The residues, deriving from the two batches, were purified by flash chromatography with hexane-ethyl acetate to give the title compound (352, 76% yield).

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed for 2 hour
  3. customThe solvent was evaporated under vacuum
  4. dissolutionthe crude was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried (Na2SO4)
  7. customevaporated
  8. customA second batch of this compound was prepared
  9. customwere purified by flash chromatography with hexane-ethyl acetate

出典と根拠

ORDレコード
ord-f1720cfc27794da78a3db6a7e7f88397
出典データセット
uspto-grants-2012_07
特許番号
US08222266B2

反応ノート

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