Sodium Hydroxide → HCID 86698279, compound

HRID 2408962Notes

Reaction equation

HRID 2408962 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.[NH2:16][C:17]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[Se:19][C:18]=1[C:26]([NH2:28])=[O:27].[OH-].[Na+].[K+].[Br-]>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[NH:16][C:17]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:23])[CH3:24])[Se:19][C:18]=1[C:26]([NH2:28])=[O:27]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 253877Potassium BromideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 866468893-Amino-5-tert-butylselenophene-2-carboxamide

Product 1

HCID 86698279HCID 86698279, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-6,7-dimethoxyquinazoline (500 mg, 2.23 mmol) in DMF (20 mL) was added sequentially 3-amino-5-tert-butylselenophene-2-carboxamide (820 mg, 3.34 mmol), powdered NaOH (270 mg, 6.69 mmol) and catalytic amount of KI at rt and the mixture was stirred at rt for 16 h. The mixture was poured into ice cooled water and stirred for 10 min. The solid separated was filtered, washed with water and dried (730 mg, 76%). The crude product was further chromatographed and recrystallized from chloroform-methanol to give the product as a pale yellow color solid, mp 248-252° C. IR (KBr) vmax 3470, 3134, 2960, 1626, 1577, 1469, 1385, 1238, 1211, 1133, 1010, 856, 750 cm−1; 1H NMR (400 MHz, DMSO-d6): δ 12.65 (1H, s, exchangeable with D2O), 8.74 (1H, s), 8.62 (1H, s), 7.64 (2H, br s, exchangeable with D2O), 7.36 (1H, s), 7.25 (1H, s), 3.96 (3H, s), 3.95 (3H, s), 1.42 (9H, s); 13C NMR (100 MHz, DMSO-d6): δ 168.3, 167.5, 154.5, 153.8, 152.9, 149.4, 146.9, 146.1, 120.7, 111.8, 108.7, 107.5, 99.8, 55.9, 55.5, 36.5, 32.2; LC-MS (positive ion mode): m/z 433, 435 (M+H)+.

Workup

  1. additionThe mixture was poured into ice
  2. stirringstirred for 10 min
  3. customThe solid separated
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried (730 mg, 76%)
  7. customThe crude product was further chromatographed
  8. customrecrystallized from chloroform-methanol
  9. customto give the product as a pale yellow color solid, mp 248-252° C

Sources & evidence

ORD record
ord-f95df8e6e27e4bfc806993cc066bc85d
Source dataset
uspto-grants-2014_08
Patent number
US08815879B2

Reaction notes

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