Trifluoroacetic acid → 4(1H)-Pteridinone, 2-amino-5,6,7,8-tetrahydro-6-(methoxymethyl)-

HRID 279946Notes

Reaction equation

HRID 279946 reaction equation
C[CH2:2][O:3][C:4]([C:6]1[C:15](=O)[N:14](C2C=CC=CC=2)[C:13]2[N:12]=[C:11]([NH:23]C3C=CC=CC=3)[N:10]=[CH:9][C:8]=2[N:7]=1)=O.FC(F)(F)C(O)=[O:33]>Cl.O=[Pt]=O>[NH2:23][C:11]1[NH:10][C:9](=[O:33])[C:8]2[NH:7][CH:6]([CH2:4][O:3][CH3:2])[CH2:15][NH:14][C:13]=2[N:12]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 44453172HCID 44453172, compound

Product 1

HCID 1355463564(1H)-Pteridinone, 2-amino-5,6,7,8-tetrahydro-6-(methoxymethyl)-Yield 85%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolvent

Procedure

The pteridinone (0.5 g, 2.4×10-3 mol) previously prepared, vide supra, was hydrogenated under 1 atm of H2 in 30 mL of distilled trifluoroacetic acid over 0.02 g of PtO2 for an hour. The mixture was diluted with 25 mL of 6N HCl, filtered, and evaporated. The crude product, the tetrahydro compound, was recrystallized twice from 6N HCl/acetonitrile to give 2-amino-5,6,7,8-tetrahydro-6-methoxymethyl-4(3H)-pteridinone as a light brown solid (0.6 g, 85%): UV: (0.1N HCl) λmax 215.5 nm (19800), 264 nm (19900); IR: (KBr) 3300, 1665, 1570, 1540, 1470, 1365, 1300, 1150, 1110, 1005, 955, and 750 cm-1 ; NMR: δ (d6 -DMSO) 3.29 (s,OMe); 3.4(m, CH's); 3.6 (br s, OCH2); 8.0 (NH). Anal. calcd. for C8H13N5O2.2HCl.1/2H2O: C, 32.78; H, 5.50; N, 23.89; Cl, 24.19. Found: C, 32.75; H, 5.54; N, 23.80; Cl, 24.21.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customThe crude product, the tetrahydro compound, was recrystallized twice from 6N HCl/acetonitrile

Sources & evidence

ORD record
ord-04c948c7e64a4208885f9de0d8a84baf
Source dataset
uspto-grants-1986_05
Patent number
US04587340

Reaction notes

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