Triethylamine → 6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine

HRID 32603

反応式

HRID 32603 の反応式
I[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10]([C:12]1[N:16]([CH3:17])[CH:15]=[N:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[CH:11].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:17][N:16]1[C:12]([C:10]#[C:11][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=2[NH2:9])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=[CH:15]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 179658065-Ethynyl-1-methyl-4-phenyl-1H-imidazole2 回HCID 179658946-Iodopyrimidine-4,5-diamine2 回

生成物 1

HCID 179657996-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine収率 76.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

6-Iodopyrimidine-4,5-diamine (Intermediate 89) (50 mg), CuI (2 mg), PdCl2dppf (16 mag), 5-ethynyl-1-methyl-4-phenyl-1H-imidazole (intermediate 26) (77 mg), and triethylamine (0.33 mL) in DMF (7 mL) were mixed together and then degassed. The reaction mixture was allowed to stir at ambient temperature under an inert atmosphere for 24 hours. The reaction mixture was filtered through diatomaceous earth, washing well with DCM and then MeCN. The organics were concentrated and the residue purified by chromatography on silica eluting with DCM:MeOH (9:1) to afford the title compound as a yellow solid (47 mg, 76%);

後処理

  1. customdegassed
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washwashing well with DCM
  4. concentrationThe organics were concentrated
  5. customthe residue purified by chromatography on silica eluting with DCM:MeOH (9:1)

出典と根拠

ORDレコード
ord-d720884f28ce43b4bd80e03c3ddae8c0
出典データセット
uspto-grants-2008_09
特許番号
US07427616B2

関連ノート

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