Trifluoroacetic acid → HCID 11278790, compound

HRID 2181623Notes

Reaction equation

HRID 2181623 reaction equation
C(OC[N:10]1[C:18]2[C:17](=[O:19])[N:16]([CH3:20])[CH2:15][N:14]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[C:13]=2[N:12]=[C:11]1[CH2:29][CH3:30])C1C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[Cl:28][C:22]1[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:21]=1[N:14]1[C:13]2[N:12]=[C:11]([CH2:29][CH3:30])[NH:10][C:18]=2[C:17](=[O:19])[N:16]([CH3:20])[CH2:15]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10160760HCID 10160760, compound

Product 1

HCID 11278790HCID 11278790, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 7-benzyloxymethyl-3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one (1.3 g, 2.92 mmol), prepared by the method described in example 7, in CHCl3 (2 mL) was treated with trifluoroacetic acid (15 mL). The solution was heated at 80° C. in a pressure tube for 5 h. The mixture was then cooled to rt and was concentrated. The residue was concentrated from heptane (2×), transferred into a separatory funnel containing saturated aqueous NaHCO3 (75 mL), and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (3% methanol in CH2Cl2) to furnish 3-(2,4-dichlorophenyl)-8-ethyl-1-methyl-1,2,3,7-tetrahydro-6H-purin-6-one (900 mg, 95% yield) as a colorless solid: mp 200-201° C.; 1H NMR (300 MHz, CDCl3) δ 12.05 (s, 1H), 7.47 (d, J=2.2 Hz, 1H), 7.20 (dd, J=8.8, 2.6 Hz, 1H), 7.12 (d, J=8.4 Hz, 1H), 4.90 (s, 2H), 3.02 (s, 3H), 2.79 (q, J=7.7 Hz, 2H), 1.34 (t, J=7.7 Hz, 3H); LRMS (APCI) m/e 325.0 [(M+H)+, calcd for C14H15N15OCl2 325.1].

Workup

  1. temperatureThe mixture was then cooled to rt
  2. concentrationwas concentrated
  3. concentrationThe residue was concentrated from heptane (2×)
  4. customtransferred into a separatory funnel
  5. additioncontaining saturated aqueous NaHCO3 (75 mL)
  6. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by column chromatography on silica gel (3% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-bfea9b74a38a443eb00a41dc8896a9f9
Source dataset
uspto-grants-2005_05
Patent number
US06894045B2

Reaction notes

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