Triethylamine → 6-Benzyl-7-isobutyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile

HRID 271591ノート

反応式

HRID 271591 の反応式
Br[C:2]1[C:3]([NH:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[C:15]1([CH2:21][C:22]#[CH:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH2:21]([C:22]1[N:10]([CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]2[N:4]=[C:5]([C:8]#[N:9])[N:6]=[CH:7][C:2]=2[CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 575753BenzylacetyleneHCID 179682615-Bromo-4-isobutylamino-pyrimidine-2-carbonitrile

生成物 1

HCID 99658026-Benzyl-7-isobutyl-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile収率 40.6%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

5-Bromo-4-isobutylamino-pyrimidine-2-carbonitrile (0.39 mmol), 3-phenyl-1-propyne (0.78 mmol), dichlorobis(triphenylphosphine)palladium (II) (0.02 mmol), copper (I) iodide (0.04 mmol) and triethylamine (1.2 mmol) in DMF (3 ml) is stirred at 75° C. for 2.5 h. After the reaction mixture is treated with saturated ammonium chloride, the mixture is extracted with AcOEt. The organic layer is washed with brine, dried over magnesium sulfate and evaporated down. The crude product is applied to a column chromatography on silica gel, which is eluted with following solvents: n-hexane:AcOEt=10:1 (v/v) and n-hexane:AcOEt=8:1 (v/v). The solvent of the latter effluent is removed by evaporation and dried in vacuo to afford the title compound. yield 40.6%, Rf=0.53 (n-hexane:AcOEt=1:1).

後処理

  1. extractionthe mixture is extracted with AcOEt
  2. washThe organic layer is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated down
  5. washis eluted with following solvents
  6. customThe solvent of the latter effluent is removed by evaporation
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-bdb808e8b9404dba937cd522a775f603
出典データセット
uspto-grants-2008_11
特許番号
US07452886B2

反応ノート

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