Triethylamine → HCID 14851903, compound

HRID 1032768Notes

Reaction equation

HRID 1032768 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[C:13]([CH3:16])=[N:14][N:15]=[C:11]3[CH2:10][N:9]=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:7]=2[CH:24]=1)#[CH:2].Br[C:26]1[CH:27]=[N:28][CH:29]=[N:30][CH:31]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:8]1[C:7]2[CH:24]=[C:3]([C:1]#[C:2][C:26]3[CH:27]=[N:28][CH:29]=[N:30][CH:31]=3)[CH:4]=[CH:5][C:6]=2[N:12]2[C:13]([CH3:16])=[N:14][N:15]=[C:11]2[CH2:10][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 783445-BromopyrimidineHCID 14851900HCID 14851900, compound

Product 1

HCID 14851903HCID 14851903, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 316 mg (1 mmol) of 8-ethynyl-6-(2-fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine 200 mg (1.25 mmol) of 5-bromopyrimidine, 45 mq of triphenylphosphine, 10 mg of cuprous iodide, 0.5 ml of triethylamine and 10 ml of dimethylformamide was stirred and degassed for 10 minutes by a slow stream of argon. Palladium acetate, 15 mg, was then added and stirring under argon was continued for 24 hours. The reaction mixture was partitioned between aqueous sodium bicarbonate solution and methylene chloride. The organic layer was washed with water, dried and evaporated, at the end azeotropically with xylene. The residue was chromatographed over 20 g of silica gel (Merck 70-230 mesh) using 5% of ethanol in methylene chloride. The combined clean fractions were evaporated and the residue was crystallized from ethyl acetate to give off-white crystals of the title compound with m.p. 143°-146° C.

Workup

  1. customdegassed for 10 minutes by a slow stream of argon
  2. additionPalladium acetate, 15 mg, was then added
  3. stirringstirring under argon
  4. customThe reaction mixture was partitioned between aqueous sodium bicarbonate solution and methylene chloride
  5. washThe organic layer was washed with water
  6. customdried
  7. customevaporated, at the end azeotropically with xylene
  8. customThe residue was chromatographed over 20 g of silica gel (Merck 70-230 mesh)
  9. customThe combined clean fractions were evaporated
  10. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7e86e100ea9a4f0faa3bf65b3d279719
Source dataset
uspto-grants-1990_09
Patent number
US04959361

Reaction notes

Loading…