Methyl Acrylate → HCID 15729527, compound

HRID 373629Notes

Reaction equation

HRID 373629 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([O:30][C:31](=[O:33])[CH3:32])[CH2:19][S:20][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[NH:23][CH:24]=[N:25]4)[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.[CH3:41][O:42][C:43](=[O:46])[CH:44]=[CH2:45]>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH:18]([O:30][C:31](=[O:33])[CH3:32])[CH2:19][S:20][C:21]3[N:29]=[CH:28][N:27]=[C:26]4[C:22]=3[N:23]=[CH:24][N:25]4[CH2:45][CH2:44][C:43]([O:42][CH3:41])=[O:46])[CH2:15][CH2:16]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 24758Sodium hydrideHCID 10392462HCID 10392462, compound

Product 1

HCID 15729527HCID 15729527, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To NaH (0.02 mmol, 0.96 mg, 50% suspension in mineral oil) in DMF (5 mL) at 0° C. was added 6-(1-[1-[bis(4-fluorophenyl)methyl]piperazin-4-yl]-2-acetoxy-3-propanylthio]purine (1.0 g, 1.8 mmol) neat in portions. After stirring about 15 min, methylacrylate (1.8 mmol, 0.16 mL) was added neat at 0° C. The ice bath was removed and the mixture stirred at room temperature for 7 days. The mixture was then heated on a 60° C. oil bath for 24 h. The DMF was removed in vacuo (1 mmHg, 60° C.) and the crude residue was eluted through silica gel using 10% MeOH:CH2Cl2. Pure product was isolated (550 mg, 49.1%) as a glassy solid; mp 55°-58° C. (dec.). DCI/MS (M+1) 625; (300 MHz) 1H NMR (CDCl3) δ: 8.15 (s,1H), 8.05 (s,1H), 7.35 (m,4H), 6.95 (m,4H), 5.3 (m,1H), 4.5 (t,2H,J=6.2 Hz), 4.2 (s,1H), 3.4 and 4.0 (q of q 2H), 3.65 (s,3H), 2.91 (t,2H,J=6.1 Hz), 2.6 (d,2H,J=6.1 Hz), 2.55 and 2.35 (m,8H), 2.0 (s,3H).

Workup

  1. customThe ice bath was removed
  2. stirringthe mixture stirred at room temperature for 7 days
  3. customThe DMF was removed in vacuo (1 mmHg, 60° C.)
  4. washthe crude residue was eluted through silica gel using 10% MeOH
  5. customPure product was isolated (550 mg, 49.1%) as a glassy solid

Sources & evidence

ORD record
ord-db72b1b7cea547d49549b824d440ea91
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

Loading…