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

HRID 631196Notes

Reaction equation

HRID 631196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[N:9]=[CH:8][NH:7][C:6]2=O.O=P(Cl)(Cl)[Cl:21]>C1(C)C=CC=CC=1>[Cl:21][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 135407708HCID 135407708, compound

Product 1

HCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
125 °C

Procedure

According to the procedure described in Example 6A Step 5, a mixture of 6-methoxy-7-(2-methoxyethoxy)quinazolin-4(3H)-one (7.83 g, 31.3 mmol) and POCl3 (20 mL) in toluene (50 mL) was heated at 125° C. for 5 hours, to afford 4-chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline as a solid (8.098 g, 96%). 1H NMR (300 MHz, DMSO-d6) δ 8.88 (s, 1H), 7.49 (s, 1H), 7.41 (s, 1H), 4.36 (t, 2H), 4.01 (s, 3H), 3.76 (t, 2H), 3.34 (s, 3H).

Sources & evidence

ORD record
ord-901b4bc79c034cac86d57086fee1505e
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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