Formaldehyde → 6-Dimethylaminomethyl-2-[4-(4-fluorobenzoyl) benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

HRID 1291313Notes

Reaction equation

HRID 1291313 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([C:8]2[CH:25]=[CH:24][C:11]([CH2:12][S:13][C:14]3[NH:15][C:16](=[O:23])[C:17]4[CH:22]=[CH:21][NH:20][C:18]=4[N:19]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[CH2:28]=O.[CH3:30][NH:31][CH3:32].O>C(O)(=O)C.O>[CH3:30][N:31]([CH2:28][C:21]1[NH:20][C:18]2[N:19]=[C:14]([S:13][CH2:12][C:11]3[CH:24]=[CH:25][C:8]([C:6](=[O:7])[C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:27][CH:26]=4)=[CH:9][CH:10]=3)[NH:15][C:16](=[O:23])[C:17]=2[CH:22]=1)[CH3:32]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 27521Dimethylamine, hydrateHCID 1356675972-[4-(4-Fluorobenzoyl)benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 1363513026-Dimethylaminomethyl-2-[4-(4-fluorobenzoyl) benzyl]thio-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-oneYield 5.5%

Reagents, catalysts & solvents 1

HCID 21899381Acetic acid--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

In 80% acetic acid/water (15 ml) was dissolved 2-[4-(4-fluorobenzoyl)benzyl]thio-7H-pyrrolo[2,3-d]-pyrimidin-4(3H)-one (570 mg) followed by addition of 37% formalin (244 mg) and, then, 50% dimethylamine-water (270 mg). The mixture was stirred at 60° C. for 13 hours. The solvent was then distilled off under reduced pressure and the residue was dissolved in water (15 ml), made basic with concentrated aqueous ammonia, and extracted with chloroform. The extract was washed with saturated aqueous NaCl solution and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (silica gel; ethanol-chloroform: 1:49-ethanol (containing 7% ammonia)-chloroform=1:19-1:9) to provide the title compound (36 mg of compound A and 233 mg of compound B).

Workup

  1. distillationThe solvent was then distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in water (15 ml)
  3. extractionextracted with chloroform
  4. washThe extract was washed with saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off under reduced pressure
  7. customthe residue was purified by flash column chromatography (silica gel; ethanol-chloroform: 1:49-ethanol (containing 7% ammonia)-chloroform=1:19-1:9)

Sources & evidence

ORD record
ord-68a4efeaef2a4c83bd4a9e2aac6a8a43
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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