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Hydrochloric Acid → HCID 86698276, compound

HRID 2408999
Notes
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Reaction equation

HRID 2408999 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:16]([C:20]1[Se:24][C:23]([C:25]([NH2:27])=[O:26])=[C:22]([OH:28])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].[OH-].[Na+].Cl>CN(C=O)C.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[O:28][C:22]1[CH:21]=[C:20]([C:16]([CH3:19])([CH3:17])[CH3:18])[Se:24][C:23]=1[C:25]([NH2:27])=[O:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 86698277HCID 86698277, compound

Product 1

HCID 86698276HCID 86698276, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol) in DMF (5 mL) was added sequentially 5-tert-butyl-3-hydroxyselenophene-2-carboxamide (220 mg, 0.89 mmol), powdered NaOH (147 mg, 3.568 mmol) and catalytic amount of KI at rt and the mixture was stirred at rt for 3 h. The mixture was poured into ice cooled water, neutralized with dil. HCl and stirred for 15 min. The precipitated solid was filtered, washed with water and dried. The crude product was chromatographed over silica gel column using chloroform-methanol (95:5) as eluents to give the product as an yellow color solid (245 mg, 63%), mp 220-224° C. 1H NMR (400 MHz, CDCl3): δ 15.16 (1H, br s, exchangeable with D2O), 13.63 (1H, br s, exchangeable with D2O), 8.17 (1H, s), 7.51 (1H, s), 7.21 (1H, s), 6.87 (1H, s), 4.05 (6H, s), 1.38 (9H, s); 13C NMR (100 MHz, CDCl3): δ 175.5, 172.0, 164.8, 156.6. 155.1, 150.7, 145.9, 139.9, 118.7, 113.1, 112.7, 108.4, 103.3, 56.5, 56.3, 37.1, 32.2; LC-MS (positive ion mode): m/z 434, 436 (M+H)+.

Workup

  1. additionThe mixture was poured into ice
  2. stirringstirred for 15 min
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water
  5. customdried
  6. customThe crude product was chromatographed over silica gel column

Sources & evidence

ORD record
ord-076f3eb220e74da6a5e2eb20ea8e800c
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08815879B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes