2-Butene, 1-bromo-3-methyl- → HCID 178442266, compound

HRID 1194662Notes

Reaction equation

HRID 1194662 reaction equation
[Na].[CH3:2][N:3]1[C:11]2[N:10]=[C:9]3[N:12]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:13](=[O:17])[CH:14]=[C:15]([OH:16])[N:8]3[C:7]=2[C:6](=[O:26])[N:5]([CH3:27])[CH2:4]1.Br[CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32]>C(O)C>[CH3:2][N:3]1[C:11]2[N:10]=[C:9]3[N:12]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[C:13](=[O:17])[C:14]([CH2:29][CH:30]=[C:31]([CH3:33])[CH3:32])=[C:15]([OH:16])[N:8]3[C:7]=2[C:6](=[O:26])[N:5]([CH3:27])[CH2:4]1

Participants

5

Reactant 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 5360545SodiumHCID 178481264HCID 178481264, compound

Product 1

HCID 178442266HCID 178442266, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolve 1.48 g (0.0644 mole) of sodium metal in 450 ml of ethanol (2B; anhydrous). Add 23.0 g (0.0644 mole) of 2,3-dihydro-1,3-dimethyl-9-(4-fluorobenzyl)-6-hydroxy-pyrimido[2,1-f]purine-4,8(1H,9H)-dione. Stir the resultant suspension under a nitrogen atmosphere for 0.5 hour, then add 9.60 g (0.0644 mole) of 1-bromo-3-methyl-2-butene. Stir the mixture at room temperature for 90 hours under a nitrogen atmosphere. Filter off the white solids, and remove solvent from the filtrate under reduced pressure. Dissolve the residue in 150 ml of chloroform, add 125 ml of 3N hydrochloric acid and shake the mixture. Separate the layers, and extract the aqueous phase with two 50-ml volumes of chloroform. Dry the combined extracts over anhydrous magnesium sulfate, filter off the drying agent, and remove solvent from the filtrate under reduced pressure. Chromatograph the residual glassy solid on silica gel, eluting with ethyl acetate(3)-hexanes(1). Triturate the product thus obtained with hexane (125 ml per gram) and filter to obtain the title compound as a solid (mp 188°-188.5° C.).

Workup

  1. filtrationFilter off the white solids
  2. customremove solvent from the filtrate under reduced pressure
  3. dissolutionDissolve the residue in 150 ml of chloroform
  4. additionadd 125 ml of 3N hydrochloric acid and shake the mixture
  5. customSeparate the layers
  6. extractionextract the aqueous phase with two 50-ml volumes of chloroform
  7. dry with materialDry the combined extracts over anhydrous magnesium sulfate
  8. filtrationfilter off the drying agent
  9. customremove solvent from the filtrate under reduced pressure
  10. washChromatograph the residual glassy solid on silica gel, eluting with ethyl acetate(3)-hexanes(1)
  11. customTriturate the product
  12. customthus obtained with hexane (125 ml per gram)
  13. filtrationfilter

Sources & evidence

ORD record
ord-d674c6f6d05048139f3cd01ba57be2d0
Source dataset
uspto-grants-1989_03
Patent number
US04816458

Reaction notes

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