Dimethylformamide → HCID 15462514, compound

HRID 842074Notes

Reaction equation

HRID 842074 reaction equation
CNC1[C:8](C(O)=O)=[CH:7][N:6]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:4]=1.[CH3:18][N:19]([CH3:22])[CH:20]=[O:21].C1(P([N:37]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C(N(CC)CC)C>[CH3:18][N:19]1[C:20](=[O:21])[NH:37][C:8]2[C:22]1=[N:4][C:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[N:6][CH:7]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 199401P,P-Diphenylphosphinic azideHCID 22617805HCID 22617805, compound

Product 1

HCID 15462514HCID 15462514, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 4-methylamino-2-phenylpyrimidine-5-carboxylic acid (7 g) and dimethylformamide (50 ml) is added triethylamine (3.1 g) at room temperature, and the mixture is stirred for 10 minutes, and thereto is added diphenylphosphoryl azide (8.4 g) at the same temperature. The reaction mixture is stirred at 120° C. for four hours, and concentrated under reduced pressure. The residue is poured into ice-water, and the precipitates are collected by filtration, washed with water, washed with ethanol, and recrystallized from chloroform to give the desired compound (5 g).

Workup

  1. stirringThe reaction mixture is stirred at 120° C. for four hours
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is poured into ice-water
  4. filtrationthe precipitates are collected by filtration
  5. washwashed with water
  6. washwashed with ethanol
  7. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-ed21f6951dde4edab25577ad1fea982b
Source dataset
uspto-grants-2002_04
Patent number
US06372740B1

Reaction notes

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