Methanol → HCID 54709827, compound

HRID 2426262Notes

Reaction equation

HRID 2426262 reaction equation
C([O:9][C:10]1[C:15](=[O:16])[N:14]2[CH2:17][CH2:18][CH2:19][C:13]2=[N:12][CH:11]=1)(=O)C1C=CC=CC=1.[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH2:26])=[CH:23][CH:22]=1.[CH3:29][OH:30]>>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][NH:26][C:29]([C:11]2[N:12]=[C:13]3[CH2:19][CH2:18][CH2:17][N:14]3[C:15](=[O:16])[C:10]=2[OH:9])=[O:30])=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 673264-FluorobenzylamineHCID 67148182HCID 67148182, compound

Product 1

HCID 54709827HCID 54709827, compound

Procedure

To a solution of crude mixture of Methyl 3-(benzoyloxy)-4-oxo-6,7,8,9-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylate and 4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-3-yl benzoate (ratio 6:1) in dry methanol, 3 eq. of 4-fluoro-benzylamine were added. The mixture was irradiated in a microwave apparatus (140° C., 500 sec). After cooling the solvent was removed under reduced pressure. The product was isolated by preparative RP-HPLC (Symmetry Column C18, 5 μm, 19×300 mm, gradient of CH3CN/H2O+0.01% TFA). The pooled product fractions were lyophilized to afford the title compound.

Workup

  1. additionwere added
  2. customThe mixture was irradiated in a microwave apparatus (140° C., 500 sec)
  3. temperatureAfter cooling the solvent
  4. customwas removed under reduced pressure
  5. customThe product was isolated by preparative RP-HPLC (Symmetry Column C18, 5 μm, 19×300 mm, gradient of CH3CN/H2O+0.01% TFA)

Sources & evidence

ORD record
ord-03b5a6b4ad27400c8d48af8c23fb00b3
Source dataset
uspto-grants-2011_06
Patent number
US07968553B2

Reaction notes

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