Hydrochloric Acid → HCID 11994283, compound

HRID 1793809Notes

Reaction equation

HRID 1793809 reaction equation
Cl.[NH2:2][C:3]1[C:4](=[O:14])[NH:5][C:6](=[O:13])[N:7]([CH2:10][CH2:11][CH3:12])[C:8]=1[NH2:9].[OH:15][C:16]12[CH2:23][CH2:22][C:19]([C:24](O)=O)([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC.O.[OH-].[Na+].Cl>CN(C=O)C>[OH:15][C:16]12[CH2:23][CH2:22][C:19]([C:24]3[NH:2][C:3]4[C:4](=[O:14])[NH:5][C:6](=[O:13])[N:7]([CH2:10][CH2:11][CH3:12])[C:8]=4[N:9]=3)([CH2:20][CH2:21]1)[CH2:18][CH2:17]2

Participants

9

Reactant 7

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11994282HCID 11994282, compoundHCID 125601364-Hydroxybicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 11994283HCID 11994283, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,6-Diamino-1-propyl-1H-pyrimidine-2,4-dione hydrochloride salt (3.4 g) was dissolved in 80 mL of DMF along with 4-hydroxy-bicyclo[2.2.2]octane-1-carboxylic acid (2.5 g, 15 mmol). HATU (5.9 g, 1.05 eq) was added, followed by Et3N (8.30 mL, 4.05 eq). The resulting reaction mixture was stirred at rt overnight. The reaction mixture was filtered to remove some of the precipitate. The filtrate was concentrated under reduced pressure. The resulting residue was dissolved in 60 mL of H2O containing 10 eq of NaOH (5.9 g). The reaction mixture was stirred under reflux for 1 h, cooled to rt and acidified to pH2 with concentrated HCl. The resulting precipitate was collected by filtration and dried to afford 1.85 g of the xanthine derivative.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. customto remove some of the precipitate
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. stirringThe reaction mixture was stirred
  6. temperatureunder reflux for 1 h
  7. temperaturecooled to rt
  8. filtrationThe resulting precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-1db5e2e77dc84a64b70ece3365399ba4
Source dataset
uspto-grants-2006_04
Patent number
US07022686B2

Reaction notes

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