N,N-Dimethylaniline → HCID 86677066, compound

HRID 1520308Notes

Reaction equation

HRID 1520308 reaction equation
O=P(Cl)(Cl)[Cl:3].CN(C)C1C=CC=CC=1.[CH2:15]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24]([C:29]1[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=1)=[N:23][C:22]2=O)[CH2:16][CH3:17].CN(C)C1C=CC=CC=1>O=P(Cl)(Cl)Cl>[Cl:3][C:22]1[C:21]2[C:26](=[CH:27][CH:28]=[C:19]([O:18][CH2:15][CH2:16][CH3:17])[CH:20]=2)[N:25]=[C:24]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[N:23]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 86743619HCID 86743619, compoundHCID 178458207HCID 178458207, compound

Product 1

HCID 86677066HCID 86677066, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

(This method is representative of method F1, F2, F3 and F4. These three methods can be implemented in a similar way except for substitution of the appropriate chlorinating reagent, solvent and temperature) To a mixture of 6-propoxy-2-pyridin-3-yl-1H-quinazolin-4-one (1.00 g, 3.56 mmol) in POCl3 (10 mL) was added N,N-dimethylaniline (0.1 mL). The resulting mixture was stirred at 120° C. for 2 h. After the reaction was completed, POCl3 was removed in vacuo, and the residue was added to ice-water slowly. The pH was adjusted to around 7 by slowly adding NaHCO3 (sat.) at 0 (C. The resultant solid was collected and purified by chromatography on silica gel eluted with petroleum ether/ethyl acetate (v/v=4:1 to 1:1) to give 580 mg of v-a as a pale yellow solid (54.7%).

Workup

  1. customPOCl3 was removed in vacuo
  2. additionthe residue was added to ice-water slowly
  3. customThe resultant solid was collected
  4. custompurified by chromatography on silica gel
  5. washeluted with petroleum ether/ethyl acetate (v/v=4:1 to 1:1)

Sources & evidence

ORD record
ord-157d1268c90a47fa81aae65c3bd81898
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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