Aniline → HCID 18186442, compound

HRID 1357540Notes

Reaction equation

HRID 1357540 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl:15][C:16]1[N:21]=[C:20](Cl)[C:19]([C:23](=[O:28])[NH:24][CH:25]([CH3:27])[CH3:26])=[CH:18][N:17]=1>C1COCC1>[NH:1]([C:20]1[C:19]([C:23](=[O:28])[NH:24][CH:25]([CH3:26])[CH3:27])=[CH:18][N:17]=[C:16]([Cl:15])[N:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 18186492HCID 18186492, compound

Product 1

HCID 18186442HCID 18186442, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-10 °C

Procedure

A solution of aniline (0.292 ml, 3.2 mmol) and triethylamine (0.447 ml, 3.21 mmol) in THF (5 ml) was added dropwise over 10 minutes to a solution of 2,4-dichloro-5-(N-isopropylcarbamoyl)pyrimidine (Method 10, 0.75 g, 3.2 mmol) in distilled THF (8 ml) at −10° C. under nitrogen. The solution was stirred at −10° C. for 1 hour and at room temperature for 2 days. Insoluble material was removed by filtration and the filtrate was diluted with ethyl acetate (20 ml). The solution was washed with water (20 ml) and saturated sodium chloride (20 ml), and then dried. Volatile material was removed by evaporation and the residue was recrystallized from DCM to give the product as a white solid (0.34 g), which was used without characterisation.

Workup

  1. customInsoluble material was removed by filtration
  2. additionthe filtrate was diluted with ethyl acetate (20 ml)
  3. washThe solution was washed with water (20 ml) and saturated sodium chloride (20 ml)
  4. customdried
  5. customVolatile material was removed by evaporation
  6. customthe residue was recrystallized from DCM

Sources & evidence

ORD record
ord-5dde756122f1470f92629c77e1c41829
Source dataset
uspto-grants-2003_07
Patent number
US06593326B1

Reaction notes

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