Methyl iodide → HCID 88507215, compound

HRID 373630Notes

Reaction equation

HRID 373630 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH:18]([OH:30])[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.[CH3:38]I>CN(C=O)C>[OH2:30].[CH3:38][N:25]1[CH:24]=[N:23][C:22]2[C:26]1=[N:27][CH:28]=[N:29][C:21]=2[S:20][CH2:19][CH:18]([OH:30])[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([CH:10]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:16][CH2:15]1.[CH3:38][N:25]1[CH:24]=[N:23][C:22]2[C:26]1=[N:27][CH:28]=[N:29][C:21]=2[S:20][CH2:19][CH:18]([OH:30])[CH2:17][N:14]1[CH2:13][CH2:12][N:11]([CH:10]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 193951Carsatrin

Product 1

HCID 88507215HCID 88507215, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To NaH (5 mmol, 240 mg, 50% in oil, pentane washed and decanted), in DMF (7 mL) was added at -15° C. 6-[1-[1-[bis(4-fluorophenyl)methyl]piperazin-4-yl]-2-hydroxy-3-propanylthio]purine (5 mmol, 2.48 g) in DMF (15 mL) over 5 min. After stirring 1 h, methyl iodide (5 mmol, 0.32 mL) in one portion was added at 0° C. under nitrogen. After one hour, the reaction mixture was concentrated under reduced pressure (1 mm Hg, 60° C.) and the crude solid passed through silica gel using 15% MeOH: CH2Cl2 to give the desired product contaminated with DMF. The product was dissolved in CH2Cl2 (50 mL) and washed with H2O (2×50 mL), saturated brine (1×50 mL), dried over Na2SO4 and conconcentrated in vacuo to give pure product (490 mg, 19.2%) as a white glass. mp. 68°-70° C. DCI/MS (M+1)=511. (300 MHz) 1H NMR (CDCl3) δ: 8.7 (s, 1H), 7.95 (s, 1H), 7.3 (m, 4H), 6.95 (m, 4H), 4.2 (s, 1H), 4.1 (m, 1H), 3.85 (s, 3H), 3.55 (octet, 2H), 2.6 (m, 2H), 2.6 (m, 4H), 2.35 (m, 4H).

Workup

  1. waitAfter one hour
  2. concentrationthe reaction mixture was concentrated under reduced pressure (1 mm Hg, 60° C.)

Sources & evidence

ORD record
ord-84b5fe246cc44b1286c6411e4efb46f8
Source dataset
uspto-grants-1992_11
Patent number
US05164390

Reaction notes

Loading…