Carbon Dioxide → HCID 22257999, compound

HRID 1251583Notes

Reaction equation

HRID 1251583 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][N:14]1[C:19](=[O:20])[C:18]2[CH:21]=[C:22]([CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[S:23][C:17]=2[N:16]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:15]1=[O:39].[C:40](=[O:42])=[O:41].[OH-].[Na+]>O1CCCC1>[CH3:13][N:14]1[C:19](=[O:20])[C:18]2[C:21]([C:40]([OH:42])=[O:41])=[C:22]([CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[S:23][C:17]=2[N:16]([CH2:35][CH:36]([CH3:37])[CH3:38])[C:15]1=[O:39]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 14798Sodium HydroxideHCID 5282538HCID 5282538, compoundHCID 178418339Butyllithium

Product 1

HCID 22257999HCID 22257999, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.0M solution in hexanes, 1.90 ml) was added dropwise to a solution of diisopropylamine (0.069 ml) in anhydrous tetrahydrofuran (30 ml) at 0° C., under nitrogen. The solution was stirred for 5 minutes then cooled to −78° C. and a solution of 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1.50 g) in anhydrous tetrahydrofuran (15 ml) was added dropwise. After 15 minutes, the flask was transferred to a sealed bomb containing carbon dioxide pellets (2 g) and heated to 50° C. for 18 hours. The reaction mixture was cooled to room temperature then added to aqueous sodium hydroxide solution (0.25M, 75 ml) and washed with ether (2×75 ml). The aqueous layer was acidified with concentrated hydrochloric acid and extracted with ether (2×75 ml). The organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography over silica, eluting with isohexane:ethyl acetate (3:1) containing 1% acetic acid, to give the subtitle compound (0.337 g) as a solid.

Workup

  1. waitAfter 15 minutes
  2. temperatureheated to 50° C. for 18 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washwashed with ether (2×75 ml)
  5. extractionextracted with ether (2×75 ml)
  6. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography over silica
  10. washeluting with isohexane:ethyl acetate (3:1)
  11. additioncontaining 1% acetic acid

Sources & evidence

ORD record
ord-a0c69224fc6d48c3bdcadb0c219e58d7
Source dataset
uspto-grants-2002_01
Patent number
US06342502B1

Reaction notes

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