Propargyl alcohol → 3-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-ol

HRID 1049842

反応式

HRID 1049842 の反応式
Br[C:2]1[NH:11][C:5]2[N:6]=[CH:7][N:8]=[C:9]([Cl:10])[C:4]=2[CH:3]=1.[O:12]1C[CH2:15][CH2:14][CH2:13]1.C(O)C#C.C(N(CC)C(C)C)(C)C>[Cu]I.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.O>[Cl:10][C:9]1[C:4]2[CH:3]=[C:2]([C:15]#[C:14][CH2:13][OH:12])[NH:11][C:5]=2[N:6]=[CH:7][N:8]=1

参加物

8

反応物 4

HCID 7859Propargyl alcoholHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 457898276-Bromo-4-chloro-7H-pyrrolo[2,3-D]pyrimidine

生成物 1

HCID 900835623-(4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-2-propyn-1-ol収率 31%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

実験手順

A mixture comprising 3.00 g (12.9 mmol) 6-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS-No: 784150-41-0), 90 mL tetrahydrofuran, 3.0 mL prop-2-yn-1-ol, 246 mg copper(I) iodide, 746 mg tetrakis(triphenylphosphine)palladium(0) and 3.93 mL N,N-diisopropylethylamine was heated at 80° C. for 4 hours. Water was added and the mixture extracted with ethylacetate/methanol (8:2). The organic layer was washed with brine and dried over sodium sulfate. After filtration and removal of the solvents the residue was purified by chromatography to give 833 mg (31%) of the title compound.

後処理

  1. extractionthe mixture extracted with ethylacetate/methanol (8:2)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration and removal of the solvents the residue
  5. customwas purified by chromatography

出典と根拠

ORDレコード
ord-1618b8364f504ed0a1a3c6b0504bf920
出典データセット
uspto-grants-2016_07
特許番号
US09382255B2

関連ノート

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