Acetic Acid → HCID 135833481, compound

HRID 279945Notes

Reaction equation

HRID 279945 reaction equation
[NH2:1][C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][O:14][CH3:15])[N:8]=2)[N:3]=1.C(O)(=[O:18])C>[OH-].[Na+]>[NH2:1][C:2]1[NH:11][C:10](=[O:18])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][O:14][CH3:15])[N:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 3234202,4-Diamino-6-methoxymethylpteridine

Product 1

HCID 135833481HCID 135833481, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The diaminopteridine, vide supra, was hydrolyzed in 1N NaOH at 70° C. for 3 hr. The resulting basic solution was then acidified with acetic acid, and the yellow product was filtered, washed with 95% ethanol and ethyl ether, and dried under vacuum overnight to yield 0.5 g (83%) of 2-amino-6-methoxymethyl-4(3H)-pteridinone as a yellow powder: UV (0.1N NaOH) λmax 255 nm (22300), 277.5 nm sh (6200), 364 nm (7100); NMR: δ (d6 -DMSO) 3.36 (s, OMe); 4.53 (s, CH2O); 7.32 (br s, NH2); and 8.63 (s, 7-H). Anal. calcd. for C8H9N5O2.7/10H2O: C, 43.72; H, 4.77; N, 31.86. Found: C, 43.77; H, 4.77; N, 31.63.

Workup

  1. filtrationthe yellow product was filtered
  2. washwashed with 95% ethanol and ethyl ether
  3. customdried under vacuum overnight

Sources & evidence

ORD record
ord-958675c265e74c85adfe8c790e963ffb
Source dataset
uspto-grants-1986_05
Patent number
US04587340

Reaction notes

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