Phosphorus oxychloride → Ethyl 4-chloro-7-iodoquinazoline-2-carboxylate

HRID 1801905Notes

Reaction equation

HRID 1801905 reaction equation
[I:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:9]2)=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:6]1[C:5]2[C:10](=[CH:11][C:2]([I:1])=[CH:3][CH:4]=2)[N:9]=[C:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136386213Ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate

Product 1

HCID 86649053Ethyl 4-chloro-7-iodoquinazoline-2-carboxylateYield 48%

Conditions

Temperature
110 °C

Procedure

A suspension of ethyl 7-iodo-4-oxo-3,4-dihydroquinazoline-2-carboxylate (1.0 g, 2.90 mmol) in phosphorus oxychloride (10 mL) was heated at 110° C. under argon for 12 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The residue was purified by column chromatography using silica gel eluting with 30% EtOAc/hexanes to afford ethyl 4-chloro-7-iodoquinazoline-2-carboxylate as a white solid (0.510 g, 48%). 1H NMR (300 MHz, DMSO-d6) δ 1.32 (t, 3H), 4.48 (q, 2H), 7.88 (d, 1H), 7.92 (d, 1H), 8.25 (s, 1H); LC-MS (ESI) m/z 363 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d025e058a08f46afbd08caface4df263
Source dataset
uspto-grants-2013_01
Patent number
US08349851B2

Reaction notes

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