Sodium Hydroxide → 1,3-Dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1h-purine-8-carboxylic acid

HRID 18573Notes

Reaction equation

[OH:1][CH2:2][C:3]1[NH:11][C:10]2[C:9](=[O:12])[N:8]([CH3:13])[C:7](=[O:14])[N:6]([CH3:15])[C:5]=2[N:4]=1.[OH-].[Na+].[O-:18][Mn](=O)(=O)=O.[K+]>O>[CH3:13][N:8]1[C:9](=[O:12])[C:10]2[NH:11][C:3]([C:2]([OH:18])=[O:1])=[N:4][C:5]=2[N:6]([CH3:15])[C:7]1=[O:14]

Participants

Conditions

Temperature: 5 °C

Procedure

5.00 g (24.0 mmol) 8-Hydroxymethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione were suspended in 15 mL water. 16.8 mL (33.6 mmol) of a 2 N NaOH-solution were added. The resulting mixture was cooled to 5° C. At that temperature a solution of 5.05 g (32.2 mmol) KMnO4 in 86 mL water was added. After stirring at room temperature for 4 h the reaction mixture was filtered over Celite. After addition of activated carbon the filtrate was again filtered over Celite. The filtrate was concentrated to a volume of 200 mL and 5 mL of conc. HCl-solution were added. After standing at 4° C. for 16 h the crystaline product was filtered off, washed twice with cold water and acetone and dried under reduced pressure at 40° C.

Workup

filtrationwas filtered over Celite
additionAfter addition of activated carbon the filtrate
filtrationwas again filtered over Celite
concentrationThe filtrate was concentrated to a volume of 200 mL and 5 mL of conc. HCl-solution
additionwere added
waitAfter standing at 4° C. for 16 h
filtrationthe crystaline product was filtered off
washwashed twice with cold water and acetone
customdried under reduced pressure at 40° C.

Sources & evidence

ORD record: ord-3bcd119c0dbc403f9e591a76a8e371e3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741341B2

Reaction notes

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