4-Chloro-6-nitroquinazoline → HCID 86698288, compound

HRID 2408969Notes

Reaction equation

HRID 2408969 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:15]([C:19]1[Se:23][C:22]([C:24]([NH2:26])=[O:25])=[C:21]([NH2:27])[CH:20]=1)([CH3:18])([CH3:17])[CH3:16]>C(O)(C)C>[N+:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][N:3]=[C:2]2[NH:27][C:21]1[CH:20]=[C:19]([C:15]([CH3:18])([CH3:16])[CH3:17])[Se:23][C:22]=1[C:24]([NH2:26])=[O:25])([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 113562574-Chloro-6-nitroquinazolineHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Product 1

HCID 86698288HCID 86698288, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 4-chloro-6-nitroquinazoline (1.1 g, 5.2 mmol) in isopropanol (10 mL) was added 5-tert-butyl-3-amino-selenophene-2-carboxamide (2.58 g, 10.50 mmol) at rt and the mixture was stirred for 30 min. The mixture was poured into ice cold water and stirred for 15 min The precipitated solid was filtered, washed with water and dried to give the product as a pale yellow color solid (2.1 g, 95%), mp 280-282° C. 1H NMR (400 MHz, DMSO-d6): δ 13.23 (1H, br s), 9.05 (1H, br s), 8.85 (1H, s), 8.56-8.60 (2H, m), 7.98 (1H, d, J=9.2 Hz), 7.80 (2H, br s), 1.43 (9H, s); LC-MS (negative ion mode): m/z 416, 418 (M−H)−.

Workup

  1. additionThe mixture was poured into ice cold water
  2. stirringstirred for 15 min The precipitated solid
  3. filtrationwas filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-dccd8eaaba95447cb7182fb6271cb168
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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