N,N-Dimethyl-1,3-propanediamine → HCID 22393272, compound

HRID 1071349Notes

Reaction equation

HRID 1071349 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][CH2:5][NH2:6].[NH2:8][C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([S:24](F)(=[O:26])=[O:25])=[CH:20][CH:19]=2)[N:10]=1>>[NH2:8][C:9]1[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([S:24](=[O:26])(=[O:25])[NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])=[CH:22][CH:23]=2)[N:10]=1

Participants

3

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 22393274HCID 22393274, compound

Product 1

HCID 22393272HCID 22393272, compoundYield 55%

Conditions

Temperature
90 °C

Procedure

3-Dimethylaminopropylamine (3 ml) was added to 4-amino-5-cyano-2-(4-fluorosulphonylanilino)pyrimidine (Method 1; 250 mg, 0.853 mmol), the mixture was heated at 90° C. for 45 minutes then stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and residue was purified by chromatography on silica gel eluting with ethyl acetate/hexane/methanol (50:50:0) increasing in polarity to (80:0:20). The product was triturated with ether and a few drops of methanol and the resulting solid collected by filtration to give the title compound (176 mg, 55%). NMR: 1.45 (t, 2H), 2.04 (s, 6H), 2.10 (t, 2H), 2.72 (t, 2H), 7.60 (s, 2H), 7.62 (d, 2H), 7.98 (d, 2H), 8.40 (s, 1H); m/z 376 (MH)+.

Workup

  1. customThe volatiles were removed by evaporation and residue
  2. customwas purified by chromatography on silica gel eluting with ethyl acetate/hexane/methanol (50:50:0)
  3. temperatureincreasing in polarity to (80:0:20)
  4. customThe product was triturated with ether and a few drops of methanol
  5. filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record
ord-dcf04e591a2e4ded87090f9194aa9563
Source dataset
uspto-grants-2005_06
Patent number
US06906065B2

Reaction notes

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