Acetic Acid → HCID 69873437, compound

HRID 1699362Notes

Reaction equation

HRID 1699362 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:30])=[CH:5][C:6]=1[C:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[N:10]2[CH:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:22](=[O:24])[CH:23]=[C:9]2[N:8]=1.C=O.[C:33](O)(=O)[CH3:34]>>[CH3:1][C:2]1[O:3][C:4]([CH3:30])=[CH:5][C:6]=1[CH:7]1[CH:12]=[C:11]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[F:20])[N:10]2[CH:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:22](=[O:24])[CH:23]=[C:9]2[N:8]1[CH2:11][N:10]([CH3:21])[CH2:9][CH2:23][C:33]1[CH:34]=[CH:2][CH:6]=[CH:7][N:8]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 18319889HCID 18319889, compound

Product 1

HCID 69873437HCID 69873437, compound

Procedure

2-(2,5-Dimethyl-3-furyl)-6-ethoxycarbonyl-4-(2-fluorophenylmethyl)-pyrrolo[1,2-a]pyrimid-7-one (50 mg, 122 umol) was added into a solution of formaldehyde (5 μL, 184 μmol) and a secondary amine (184 μmol) in acetic acid (2 mL). The resulting solution was stirred at room temperature for ten minutes, and then 50° C. for another ten minutes. HOAc was evaporated and the residue was diluted with DCM and purified by prep-TLC (MeOH/DCM−1:9) to yield the desired product, which was characterized by proton NMR and mass spectra.

Workup

  1. wait50° C. for another ten minutes
  2. customHOAc was evaporated
  3. additionthe residue was diluted with DCM
  4. custompurified by prep-TLC (MeOH/DCM−1:9)

Sources & evidence

ORD record
ord-428ca840e45a410688f801dc64881522
Source dataset
uspto-grants-2002_02
Patent number
US06346534B1

Reaction notes

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