Methanol → 3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile

HRID 600440노트

반응식

HRID 600440 반응식
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH:10][C:11]1[N:19]=[C:18]2[C:14]([NH:15][C:16](=[O:20])[NH:17]2)=[C:13]([Cl:21])[N:12]=1.CO.[CH3:24]OC(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1>CS(C)=O>[Cl:21][C:13]1[N:12]=[C:11]([N:10]2[C:3]3[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=3[N:1]=[CH:24]2)[N:19]=[C:18]2[C:14]=1[NH:15][C:16](=[O:20])[NH:17]2

참가 물질

6

반응물 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 866229404-amino-3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)benzonitrile

생성물 1

HCID 576127423-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-yl)-3H-benzo[d]imidazole-5-carbonitrile수율 67%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of crude 4-amino-3-(6-chloro-8-oxo-8,9-dihydro-7H-purin-2-ylamino)benzonitrile (1.23 mmol) in anhydrous DMSO (10 mL) was added methanol (150 mL), followed by anhydrous trimethylorthoformate (5 mL) and p-toluene sulfonic acid (100 mg) and the reaction mixture was stirred under Ar at room temperature for 3 h (LC-MS monitoring). The solvent was removed in vacuo and the residue redissolved in 7 mL of DMSO, then 40 mL of water were added. The pink solid formed was filtered under vacuo using a fine porosity Buchner filter funnel, washed with water, then dried in the vacuum oven at 60° C. to give 0.26 g of the desired product (67% yield on 2 steps). 1H NMR (300 MHz, CDCl3+CD3OD) δ, ppm: 9.24 (s, 1H), 9.00 (s, 1H), 7.91 (d, 1H), 7.69 (d, 1H); MS (EI) m/z 312.2 (MH)+.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue redissolved in 7 mL of DMSO
  3. addition40 mL of water were added
  4. customThe pink solid formed
  5. filtrationwas filtered under vacuo
  6. filtrationfilter funnel
  7. washwashed with water
  8. customdried in the vacuum oven at 60° C.

출처 및 근거

ORD 기록
ord-d74f7c1cd85b43a4a62f25b083257c3f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902187B2

반응 노트

불러오는 중…