4-Methylmorpholine → [4-Chloro-6-quinazolinyl]-2-butynamide

HRID 583099Notes

Reaction equation

HRID 583099 reaction equation
[C:1]([OH:6])(=O)[C:2]#[C:3][CH3:4].ClC(OCC(C)C)=O.C[N:16]1CCOCC1.N[C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][N:27]=[C:26]2[Cl:33].C(=O)(O)[O-].[Na+]>O1CCCC1.[Cl-].[Na+].O>[Cl:33][C:26]1[C:25]2[C:30](=[CH:31][CH:32]=[C:23]([CH2:4][C:3]#[C:2][C:1]([NH2:16])=[O:6])[CH:24]=2)[N:29]=[CH:28][N:27]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 685352-Butynoic acidHCID 516892Sodium BicarbonateHCID 183506914-Chloroquinazolin-6-amine

Product 1

HCID 54436052[4-Chloro-6-quinazolinyl]-2-butynamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 1.64 g of 2-butynoic acid in 46 ml of tetrahydrofuran was cooled in an ice bath. A 2.34 ml portion of isobutyl chloroformate followed by a 4.13 ml portion of N-methyl morpholine were added. After about 10 minutes, this was poured into a solution of 6-amino-4-chloroquinazoline in 46 ml tetrahydrofuran. This mixture was stirred at room temperature for 2 hours. The mixture was poured into a mixture of brine and saturated sodium bicarbonate and extracted with ether. The ether solution was dried over magnesium sulfate and filtered. The solvent was removed giving [4-chloro-6-quinazolinyl]-2-butynamide as colored oil that was used in the next step without additional purification.

Workup

  1. additionwere added
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-71205d2d9c5549428480c346307f71d4
Source dataset
uspto-grants-1999_07
Patent number
US05929080

Reaction notes

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