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

HRID 32603

반응식

HRID 32603 반응식
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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 179658065-Ethynyl-1-methyl-4-phenyl-1H-imidazole2회HCID 179658946-Iodopyrimidine-4,5-diamine2회

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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%);

후처리

  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)

출처 및 근거

ORD 기록
ord-d720884f28ce43b4bd80e03c3ddae8c0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427616B2

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