Hydrochloric Acid → HCID 11529870, compound

HRID 2381014Notes

Reaction equation

HRID 2381014 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]=[C:5]2[N:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14].O.[CH2:24]=O.[C:26]([BH3-])#[N:27].[Na+].Cl>CCOC(C)=O>[CH3:24][N:27]([CH3:26])[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[N:6]=[C:5]2[N:13]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH3:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 11471935HCID 11471935, compoundHCID 22136924Formaldehyde--water (1/1)

Product 1

HCID 11529870HCID 11529870, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of (6-amino-2-methyl-quinazolin-4-yl)-(4-methoxy-phenyl)-methylamine (16 mg, 0.05 mmol), 2 ml of 37% formaldehyde water solution and sodium cyanoborohydride (6.3 mg, 0.1 mmol) was added 2 N HCl (0.05 ml) at 0° C. The reaction mixture was stirred for 1 h at 0° C., then diluted by EtOAc (10 ml), washed with saturated NaHCO3 aq., brine, dried over Na2SO4, filtered and concentrated by vacuum. The crude product was purified by chromatography on silica gel with acetate, hexane (1:3 to 1:1) as eluent, yielding 11 mg of title compound (68.8%) as yellow solids. 1H NMR (CDCl3): 7.63 (d, J=9.0 Hz, 1H), 7.20-7.12 (m, 3H), 6.91-6.88 (m, 2H), 6.23 (d, J=2.7 Hz, 1H), 3.80 (s, 3H), 3.57 (s, 3H), 2.69 (s, 3H), 2.62 (s, 6H).

Workup

  1. washwashed with saturated NaHCO3 aq., brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated by vacuum
  5. customThe crude product was purified by chromatography on silica gel with acetate, hexane (1:3 to 1:1) as eluent

Sources & evidence

ORD record
ord-27c80419853e4f60959d5ce178929af3
Source dataset
uspto-grants-2012_09
Patent number
US08258145B2

Reaction notes

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