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

HRID 1068968Notes

Reaction equation

HRID 1068968 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-21927f0a90804e41b6e10544d4e70a26
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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