Carbon Dioxide → 2-(4,6-Dimethoxypyrimidin-2-yl)acetic acid

HRID 1034407Notes

Reaction equation

HRID 1034407 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=1.[C:24](=[O:26])=[O:25]>O1CCCC1.O>[CH3:22][O:21][C:19]1[CH:20]=[C:15]([O:14][CH3:13])[N:16]=[C:17]([CH2:23][C:24]([OH:26])=[O:25])[N:18]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 7912DiisopropylamineHCID 110409044,6-Dimethoxy-2-methylpyrimidineHCID 178418339Butyllithium

Product 1

HCID 124207552-(4,6-Dimethoxypyrimidin-2-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (200 ml of 2N in pentane) was added dropwise over 30 minutes to a stirred solution of di-isopropylamine (40.4 g) in tetrahydrofuran (200 ml) at -70° C. under nitrogen. The mixture was stirred for 20 minutes and then 4,6-dimethoxy-2-methylpyrimidine (61.6 g) in tetrahydrofuran (200 ml) was added dropwise over 20 minutes. The mixture was stirred at -70° C. for 30 minutes before being poured onto a large excess of solid carbon dioxide. The mixture was allowed to warm to room temperature before water (800 ml) was added. The clear solution was concentrated to half volume under vacuum and was then washed with ether. The aqueous phase was acidified with concentrated hydrochloric acid and the resulting solid was filtered, washed with water and dried to give 58.3 g of (4,6-dimethoxypyrimidin-2-yl)acetic acid.

Workup

  1. stirringThe mixture was stirred at -70° C. for 30 minutes
  2. additionwas added
  3. concentrationThe clear solution was concentrated to half volume under vacuum
  4. washwas then washed with ether
  5. filtrationthe resulting solid was filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-95ac3b421ca64c258b0b77b67ad52b3e
Source dataset
uspto-grants-1994_05
Patent number
US05317005

Reaction notes

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