Water → HCID 71743940, compound

HRID 2280998Notes

Reaction equation

HRID 2280998 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[N:13]O)=[C:8]2[C:3]=1[CH:4]=[N:5][CH:6]=[N:7]2.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC.O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]([C:12]#[N:13])=[C:8]2[C:3]=1[CH:4]=[N:5][CH:6]=[N:7]2

Participants

5

Reactant 3

HCID 962WaterHCID 111923Propylphosphonic anhydrideHCID 1317335108-Quinazolinecarboxaldehyde, 5-bromo-, oxime

Product 1

HCID 71743940HCID 71743940, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
100 °C

Procedure

To a solution of 5-Bromo-quinazoline-8-carbaldehyde oxime (3000.00 mg; 11.90 mmol; 1.00 eq.) in DMF (15 ml) was added 2,4,6-Tripropyl-[1,3,5,2,4,6]trioxatriphosphinane 2,4,6-trioxide (10.42 ml; 17.85 mmol; 1.50 eq.) 50% in DMF. The resulting mixture was stirred at 100° C. for 45 min, LCMS showed major peak (MS: 252/254, 234/236) and small (MS: 208/209). The reaction mixture was cooled, poured into water, extracted with EtOAc, dried and concentrated to yield sticky solid, which was washed with ether to collected the title product (1665 mg. yield 59.6%). LC-MS (232/234 and 250/252).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. customdried
  4. concentrationconcentrated
  5. customto yield sticky solid, which
  6. washwas washed with ether

Sources & evidence

ORD record
ord-e3b4570d84cc41c2acfc099b103e0ae7
Source dataset
uspto-grants-2015_09
Patent number
US09139568B2

Reaction notes

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