Hydrochloric Acid → HCID 66847070, compound

HRID 254180Notes

Reaction equation

HRID 254180 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[N:8]=[C:7]([C:9]#N)[CH:6]=[C:5]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:4]=1.Cl.C1C[O:22]CC1.[Li+:24].[OH-:25]>O.CO>[Li+:24].[CH3:1][N:2]([CH3:17])[C:3]1[N:8]=[C:7]([C:9]([O-:22])=[O:25])[CH:6]=[C:5]([C:11]2[O:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:4]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 11253171HCID 11253171, compound

Product 1

HCID 66847070HCID 66847070, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-dimethylamino-6-(5-methylfuran-2-yl)pyrimidine-4-carbonitrile (0.68 g, 2.98 mmol) in 6-M HCl (40 mL) and THF (10 mL) was refluxed for 6 h, cooled, concentrated in vacuo and the residue subjected to ion-exchange column chromatography (Isolute® Flash SCX-2; DCM; MeOH then 1-M NH3:MeOH). The resulting mixture of methyl ester and carboxylic acid (0.42 g) was treated with MeOH (15 mL), water (15 mL) and LiOH (72 mg, 1.81 mmol), stirred at room temperature for 1 h and concentrated in vacuo to give the title compound (0.48 g, 98%) as a white solid: NMR δH (400 MHz, CD3OD) 2.38 (3H, s), 3.23 (6H, s), 6.19-6.20 (1H, m), 7.08-7.09 (1H, m) and 7.31 (1H, s); M/Z 248 (M+H)+

Workup

  1. temperaturewas refluxed for 6 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additionThe resulting mixture of methyl ester and carboxylic acid (0.42 g)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a27a6fdb8a2148a89d46db81643881b0
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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