Sodium Hydroxide → HCID 66859447, compound

HRID 2171306Notes

Reaction equation

HRID 2171306 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[NH:10][CH:9]=[C:8]([C:11]([O:13]CC)=[O:12])[C:7](=[O:16])[N:6]2[CH:17]=1)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([C:3]1[CH:4]=[C:5]2[NH:10][CH:9]=[C:8]([C:11]([OH:13])=[O:12])[C:7](=[O:16])[N:6]2[CH:17]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66858915Ethyl 7-ethyl-4-oxo-1,4-dihydropyrrolo[1,2-a]pyrimidine-3-carboxylate

Product 1

HCID 66859447HCID 66859447, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 7-ethyl-4-oxo-1,4-dihydropyrrolo[1,2-a]pyrimidine-3-carboxylate (0.63 g, 2.711 mmol) was dissolved in a solution of methanol (8 mL)/sodium hydroxide (13.56 mL, 2.0 M, 27.11 mmol) and heated at reflux for 3 hours. The mixture was allowed to cool to room temperature and methanol was removed in vacuo. The aqueous solution was cooled to 0° C. and concentrated HCl was slowly added until a precipitate formed (pH 4). The precipitate was filtered, washed with water and dried to give 7-ethyl-4-oxo-1,4-dihydropyrrolo[1,2-a]pyrimidine-3-carboxylic acid; 0.43 g (77%). LC/MS (10-99% CH3CN/0.05% TFA in H2O/0.05% TFA gradient over 3 min): M+H m/z 207.1, retention time 1.10 minutes. 1H NMR (400.0 MHz, DMSO) δ 13.42 (bs, 1H), 12.89 (bs, 1H), 8.51 (s, 1H), 7.29 (t, J=0.8 Hz, 1H), 6.17 (d, J=1.8 Hz, 1H), 2.61-2.50 (m, 2H) and 1.20 (t, J=7.5 Hz, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. custommethanol was removed in vacuo
  4. temperatureThe aqueous solution was cooled to 0° C.
  5. additionconcentrated HCl was slowly added until a precipitate
  6. customformed (pH 4)
  7. filtrationThe precipitate was filtered
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-15afe1912f4243e88b823d05871c4d4a
Source dataset
uspto-grants-2015_06
Patent number
US09051324B2

Reaction notes

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