Sodium hydride → 125345-93-9

HRID 2352431Notes

Reaction equation

HRID 2352431 reaction equation
[H-].[Na+].[SH:3][C:4]1[N:12]=[CH:11][N:10]=[C:9]2[C:5]=1[NH:6][CH:7]=[N:8]2.[O:13]1[C@@H:15]([CH3:16])[CH:14]1[N:17]1[CH2:22][CH2:21][N:20]([CH:23]([C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>CN(C=O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([CH:23]([C:31]2[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=2)[N:20]2[CH2:19][CH2:18][N:17]([CH2:14][C@H:15]([OH:13])[CH2:16][S:3][C:4]3[N:12]=[CH:11][N:10]=[C:9]4[C:5]=3[NH:6][CH:7]=[N:8]4)[CH2:22][CH2:21]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86743481HCID 86743481, compoundHCID 178527888HCID 178527888, compound

Product 1

HCID 72049125345-93-9

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To NaH (0.56 g, 11.6 mmol, 50% suspension in mineral oil prewashed with pentane) in DMF (12 mL) at 0° C. 6-mercaptopurine (1.97 g, 11.6 mmol) was added in portions over 10 min. (2S)-(-)-(1,2-Epoxypropyl)-4-[bis(4-fluorophenyl)methyl]piperazine (4.0 g, 11.6 mmol) in DMF (10 mL) was added dropwise at 0° C. over a 5 min period. The reaction mixture was allowed to warm to room temperature after an additional 5 min and was stirred for 72 h. DMF was removed in vacuo (1 mm Hg, 55° C.) and the residue was dissolved in CH2Cl2 (100 mL). The solution was filtered through celite, concentrated and the residue was purified by flash chromatography on silica gel using 10% MeOH:CH2Cl2 to give the title compound as a white solid, 1.37 g (23%), mp 118°-120° C. (dec.); DCI/MS (M+1) 497. 400 MHz 1H NMR (CDCl3) δ: 8.65 (s, 1H), 8.2 (s, 1H), 7.35 (m, 4H), 6.98 (m, 4H), 4.2 (s, 1H), 4.18 (m, 1H), 3.65-3.45 (m, 2H), 2.7-2.4 (m, 10H); [δ]D22 +7.3° (0.5% in EtOH).

Workup

  1. customat 0° C
  2. additionwas added dropwise at 0° C. over a 5 min period
  3. customDMF was removed in vacuo (1 mm Hg, 55° C.)
  4. dissolutionthe residue was dissolved in CH2Cl2 (100 mL)
  5. filtrationThe solution was filtered through celite,
  6. concentrationconcentrated
  7. customthe residue was purified by flash chromatography on silica gel using 10% MeOH

Sources & evidence

ORD record
ord-fc92e971398846d89a804665694edbd8
Source dataset
uspto-grants-1989_10
Patent number
US04876257

Reaction notes

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