Potassium Hydroxide → HCID 56656534, compound

HRID 1469008Notes

Reaction equation

HRID 1469008 reaction equation
[CH3:1][N:2]([CH3:30])[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=2)[N:6]=[C:5]([N:20]2[CH:24]=[C:23]([C:25]([O:27]CC)=[O:26])[CH:22]=[N:21]2)[N:4]=1.[OH-].[K+]>C1COCC1>[CH3:1][N:2]([CH3:30])[C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:10][CH:11]=2)[N:6]=[C:5]([N:20]2[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[CH:22]=[N:21]2)[N:4]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86686099HCID 86686099, compound

Product 1

HCID 56656534HCID 56656534, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of ethyl 1-(4-(dimethylamino)-7-phenoxyquinazolin-2-yl)-1H-pyrazole-4-carboxylate (35 mg, 0.09 mmol), 1M aqueous KOH (0.43 mL, 0.43 mmol), and THF (1.3 mL) was heated to 40° C. for 48 h with rapid stirring. The mixture was then concentrated, cooled in an ice bath, and 1M aqueous HCl was added until the mixture was slightly acidic (pH ca 5-6). The resulting precipitate was collected by filtration, washed with water, and dried to furnish the titled compound (22 mg, 68%). MS (ESI): mass calcd. for C20H17N5O3, 375.1; m/z found, 376.3 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 12.73 (s, 1H), 8.98 (d, J=0.6 Hz, 1H), 8.31 (d, J=9.3 Hz, 1H), 8.07 (s, 1H), 7.52 (ddd, J=7.6, 5.9, 2.2 Hz, 2H), 7.36-7.28 (m, 1H), 7.28-7.20 (m, 2H), 7.17 (dd, J=9.3, 2.7 Hz, 1H), 6.97 (d, J=2.7 Hz, 1H), 3.46 (s, 6H).

Workup

  1. concentrationThe mixture was then concentrated
  2. temperaturecooled in an ice bath
  3. addition1M aqueous HCl was added until the mixture
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-41aae6c34fc24d57b821fc2ec9223188
Source dataset
uspto-grants-2015_04
Patent number
US09006251B2

Reaction notes

Loading…