Phosphorus oxychloride → 4-Chloro-7-methoxy-6-(2-methoxyethoxy)quinazoline

HRID 871278Notes

Reaction equation

HRID 871278 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=O)[NH:8][CH:9]=[N:10]2)=[CH:5][C:4]=1[O:14][CH2:15][CH2:16][O:17][CH3:18].O=P(Cl)(Cl)[Cl:21]>C1(C)C=CC=CC=1>[Cl:21][C:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[C:4]([O:14][CH2:15][CH2:16][O:17][CH3:18])[CH:5]=2)[N:10]=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1355098047-methoxy-6-(2-methoxyethoxy)quinazolin-4(3H)-one

Product 1

HCID 109344884-Chloro-7-methoxy-6-(2-methoxyethoxy)quinazolineYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

According to the procedure described in Example 6A Step 5, a mixture of 7-methoxy-6-(2-methoxyethoxy)quinazolin-4(3H)-one (0.6 g, 2.4 mmol) and POCl3 (1 mL) in toluene (10 mL) was heated at 125° C. for 2 hours, to afford 4-chloro-7-methoxy-6-(2-methoxyethoxy)quinazoline as solid (0.445 g, 69%). 1H NMR (300 MHz, DMSO-d6) δ 8.88 (s, 1H), 7.45 (s, 1H), 7.41 (s, 1H), 4.33 (t, 2H), 4.03 (s, 3H), 3.77 (t, 2H), 3.33 (s, 3H).

Sources & evidence

ORD record
ord-3ca9d6d9c3f64c5b87cf7ed76a822e22
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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