Ammonia → HCID 136268151, compound

HRID 1409557Notes

Reaction equation

HRID 1409557 reaction equation
[OH:1][C:2]1[C:3]([C:21]([O:23]C)=O)=[N:4][C:5]([CH2:9][C:10]2([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:14][CH2:13][CH2:12][CH2:11]2)=[N:6][C:7]=1[OH:8].CO.[NH3:27]>>[OH:1][C:2]1[C:7](=[O:8])[NH:6][C:5]([CH2:9][C:10]2([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11][CH2:12][CH2:13][CH2:14]2)=[N:4][C:3]=1[C:21]([NH2:27])=[O:23]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 178499080HCID 178499080, compound

Product 1

HCID 136268151HCID 136268151, compoundYield 49%

Procedure

A solution of methyl 5,6-dihydroxy-2-((1-phenylcyclopentyl)methyl)pyrimidine-4-carboxylate (0.020 g, 60.9 μmol) in ammonia in MeOH (435 μl, 3.05 mmol) was heated at 100° C. for 20 min. The cooled solution was evaporated to dryness. The residue was diluted with MeOH and heated in the presence of Amberlyst resin (H+) until in solution. The material was filtered to remove the resin and evaporated to dryness. Trituration with MeOH followed by washing with Et2O provided the desired product as a white solid (0.011 g; 49%). LCMS: m/z=314 (MH+).

Workup

  1. customThe cooled solution was evaporated to dryness
  2. additionThe residue was diluted with MeOH
  3. temperatureheated in the presence of Amberlyst resin (H+) until in solution
  4. filtrationThe material was filtered
  5. customto remove the resin
  6. customevaporated to dryness
  7. washby washing with Et2O

Sources & evidence

ORD record
ord-fbab8135e34b44c58684939b27ec2d22
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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