HCID 57850035, compound → HCID 10014219, compound

HRID 736596Notes

Reaction equation

HRID 736596 reaction equation
[OH:1][CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[N+:12]([O-])=O)[N:5]=[CH:4][N:3]1[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>CCOC(C)=O.CO.[Pt]>[NH2:12][C:10]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:11]=1[CH:2]([OH:1])[N:3]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:4]=[N:5]2

Participants

4

Reactant 1

HCID 57850035HCID 57850035, compound

Product 1

HCID 10014219HCID 10014219, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

4-hydroxy-5-nitro-3-pentyl-3,4-dihydroquinazoline (6a, 10.0 g, 38.0 mmol) was dissolved in EtOAc-MeOH mixed solvent (2:1, 150 ml) and 3% Pt—C (1.0 g) was added. Hydrogenation was carried out at room temperature under H2 atmosphere using a balloon. After 2 h, the reaction was stopped and the mixture was filtered. The filtrated was concentrated under reduced pressure and the obtaining residual oil was purified by a short silica gel (100 g) column chromatography (eluent: EtOAc/MeOH=20/1) to give 5-amino-4-hydroxy-3-pentyl-3,4-dihydroquinazoline (2a, 6.56 g, 74%); 1H NMR (270 MHz) δ (CD3OD) 0.88 (t, J=6.9 Hz, 3H), 1.23-1.41 (m, 4H), 1.63-1.74 (m, 2H), 3.26-3.35 (m, 1H), 3.51-3.62 (m, 1H), 6.15 (s, 1H), 6.47-6.51 (m, 1H), 6.55 (dd, J=1.0 and 7.9 Hz, 1H), 7.06 (t, J=7.9 Hz, 1H), 7.43 (s, 1H); MS (ES) m/z 234 (M+).

Workup

  1. customwas carried out at room temperature under H2 atmosphere
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrated was concentrated under reduced pressure
  4. customthe obtaining residual oil was purified by a short silica gel (100 g) column chromatography (eluent: EtOAc/MeOH=20/1)

Sources & evidence

ORD record
ord-09c16e7f3f1e4af382171de73f2008b7
Source dataset
uspto-grants-2009_09
Patent number
US07595400B2

Reaction notes

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