Sodium Hydroxide → HCID 77230715, compound

HRID 2369813Notes

Reaction equation

HRID 2369813 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=O)[C:9]2[C:4](=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:28].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CC#N.O>[Cl:28][C:10]1[C:9]2[C:4](=[C:5]([C:13]([O:15][CH3:16])=[O:14])[CH:6]=[CH:7][CH:8]=2)[N:3]=[C:2]([CH3:1])[N:11]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 136278282HCID 136278282, compound

Product 1

HCID 77230715HCID 77230715, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of methyl 2-methyl-4-oxo-3,4-dihydroquinazoline-8-carboxylate (2.00 g; 9.17 mmol; 1.00 eq.) and benzyltriethylammonium chloride (4.18 g, 18.33 mmol) in dry CH3CN (5 mL) was treated with DIEA (1.75 mL, 10.1 mmol) and stirred as POCl3 (7.3 mL, 80.2 mmol) was slowly added to the flask. The contents were warmed to 90° C. for 30 min, cooled to ˜50° C., and slowly poured into a 2N NaOH (80 mL, 160 mmol) and water (80 mL) that was cooling in an acetone/dry-ice bath (ice formed in the flask). The off-red solid that precipitated was filtered, washed with 10% aqueous K2CO3 (15 mL), and dried under vacuum to afford 1 (1.35 g; 62% yield). LC-MS [236.8 (M+1)]

Workup

  1. additionwas slowly added to the flask
  2. temperaturecooled to ˜50° C.
  3. temperaturewas cooling in an acetone/dry-ice bath (ice
  4. customformed in the flask)
  5. filtrationThe off-red solid that precipitated was filtered
  6. washwashed with 10% aqueous K2CO3 (15 mL)
  7. customdried under vacuum
  8. customto afford 1 (1.35 g; 62% yield)

Sources & evidence

ORD record
ord-405338a3ac344c5ca6fd40c6fc8b9a26
Source dataset
uspto-grants-2014_04
Patent number
US08710044B2

Reaction notes

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