HCID 86723486, compound → HCID 86723487, compound

HRID 2201250Notes

Reaction equation

HRID 2201250 reaction equation
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([C@@H:17]([CH2:21][CH2:22][C:23]([OH:25])=O)[C:18]([OH:20])=[O:19])[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:6]2[C:5](=[O:26])[N:4]([CH3:27])[C:3]1=[O:28]>O>[CH3:1][N:2]1[C:7]2=[C:8]3[N:9]([C:10]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[C:6]2[C:5](=[O:26])[N:4]([CH3:27])[C:3]1=[O:28])[C@H:17]([C:18]([OH:20])=[O:19])[CH2:21][CH2:22][C:23]3=[O:25]

Participants

3

Reactant 1

HCID 86723486HCID 86723486, compound

Product 1

HCID 86723487HCID 86723487, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
110 °C

Procedure

(S)-2-(1,3-Dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)pentanedioic acid (2.44 g, 6.33 mmol) and polyphosphoric acid (4.85 ml, 6.33 mmol) were combined and heated at 110° C. for 85 mins. The reaction mixture was cooled to ˜50° C. and diluted with water to give a fluid mixture. The mixture was then cooled to room temperature, further diluted with water and extracted with chloroform (5×). The combined organic extracts were passed through a hydrophobic frit and evaporated under vacuum to afford the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to ˜50° C.
  2. customto give a fluid mixture
  3. temperatureThe mixture was then cooled to room temperature
  4. extractionextracted with chloroform (5×)
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-43259739edb1408c933eb3ecdc47462c
Source dataset
uspto-grants-2016_06
Patent number
US09359381B2

Reaction notes

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