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Sodium hydride → 7-[4-(4-Fluorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

HRID 1291233
Notes
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Reaction equation

HRID 1291233 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[C:13]([CH3:14])=[CH:12][NH:11][C:5]=2[N:6]=[C:7]([S:9][CH3:10])[N:8]=1.[H-].[Na+].[F:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=2)=[O:23])=[CH:20][CH:19]=1>COCCOC>[F:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28][N:11]3[C:5]4[N:6]=[C:7]([S:9][CH3:10])[N:8]=[C:3]([O:2][CH3:1])[C:4]=4[C:13]([CH3:14])=[CH:12]3)=[CH:26][CH:25]=2)=[O:23])=[CH:32][CH:33]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 47290134-(4-Fluorobenzoyl)benzyl bromideHCID 131876724-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 189190267-[4-(4-Fluorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidineYield 84%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent
2×

Procedure

Under argon gas, 4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (4.18 g) was dissolved in anhydrous DME (120 ml). Then, with ice-cooling and stirring, 60% sodium hydride-oil (0.88 g) was added in 3 installments. After completion of addition, the mixture was stirred for 30 minutes, at the end of which time a solution of 4-(4-fluorobenzoyl)benzyl bromide (6.74 g) in anhydrous DME (20 ml) was added. Then, at room temperature, the mixture was stirred for 2 hours. The solvent was distilled off under reduced pressure and the residue was dissolved in ethyl acetate, washed with saturated aqueous NaCl solution, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure, whereupon colorless needles separated out. These crystals were collected by filtration, rinsed with ethyl acetate, and dried to provide the title compound (7.07 g). 1H-NMR (CDCl3) 5: 2.33(3H,d,J=1.2Hz), 2.61(3H,s), 4.09(3H,s), 5.37(2H,s), 6.58(1H,d,J=1.2Hz), 7.15(2H,t,J=8.6Hz), 7.29(2H,d,J=8.4Hz), 7.71(2H,d,J=8.4Hz), 7.82(2H,dd,J=5.4&8.8Hz).

Workup

  1. temperatureThen, with ice-cooling
  2. additionAfter completion of addition
  3. additionwas added
  4. stirringThen, at room temperature, the mixture was stirred for 2 hours
  5. distillationThe solvent was distilled off under reduced pressure
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with saturated aqueous NaCl solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was then distilled off under reduced pressure, whereupon colorless needles
  10. customseparated out
  11. filtrationThese crystals were collected by filtration
  12. washrinsed with ethyl acetate
  13. customdried

Sources & evidence

ORD record
ord-2da37c7e70924984b42679d91acf287d
Source dataset
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05753664

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes