Potassium Carbonate → HCID 178429487, 화합물

HRID 577040노트

반응식

HRID 577040 반응식
[CH3:1][C:2]1[N:7]=[C:6]([SH:8])[N:5]=[C:4]([OH:9])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]1[N:19]=[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]2[CH:26]=1>CN(C=O)C>[N:19]1[C:18]([CH2:17][S:8][C:6]2[N:5]=[C:4]([OH:9])[CH:3]=[C:2]([CH3:1])[N:7]=2)=[CH:26][N:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=12

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 4318932-(bromomethyl)imidazo[1,2-a]pyridineHCID 178429541HCID 178429541, 화합물

생성물 1

HCID 178429487HCID 178429487, 화합물수율 52%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

6-methyl-2-sulfanylpyrimidin-4-ol (638 mg, 4.5 mmol) was dissolved in anhydrous DMF (20 mL), then potassium carbonate (1.86 g, 13.5 mmol) and 2-(bromomethyl)imidazo[1,2-a]pyridine (1.42 g, 6.7 mmol) were added. The mixture was stirred overnight at room temperature. The solid was removed by filtration and washed with methanol, where the filtrate was evaporated. The residue was dissolved in DCM/MeOH and purified on silica gel using 12% DCM/MeOH to afford 2-({imidazo[1,2-a]pyridin-2-ylmethyl}sulfanyl)-6-methylpyrimidin-4-ol as a white solid (631 mg, 52% yield); 1H NMR (400 MHz, DMSO-d6): δ 2.21 (s, 3H), 4.46 (s, 2H), 5.99 (bs, 1H), 6.84 (dt, J=1.7 Hz, J=6.7 Hz, 1H), 7.17-7.22 (m, 1H), 7.45 (dd, J=9.0 Hz, J=0.8 Hz, 1H), 7.86 (s, 1H), 8.46-8.49 (m, 1H); LRMS (ES+) m/z 273 (60%, M+1).

후처리

  1. customThe solid was removed by filtration
  2. washwashed with methanol, where the filtrate
  3. customwas evaporated
  4. dissolutionThe residue was dissolved in DCM/MeOH
  5. custompurified on silica gel using 12% DCM/MeOH

출처 및 근거

ORD 기록
ord-ac4482cb18764aa8ae82d6cbc840fbc3
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040538B2

반응 노트

불러오는 중…