Cyclobutylamine → HCID 22393266, compound

HRID 1071350Notes

Reaction equation

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

Participants

Reactant 2

HCID 75645Cyclobutylamine

HCID 22393274HCID 22393274, compound

Product 1

HCID 22393266HCID 22393266, compoundYield 31%

Conditions

Temperature: 40 °C

Procedure

Cyclobutylamine (2 ml) was added to 4-amino-5-cyano-2-(4-fluorosulphonylanilino) pyrimidine (Method 1; 250 mg, 0.853 mmol), the mixture was heated at 40° C. for 1 hour and 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 (50:50). The product was triturated with ether/hexane and the resulting solid collected by filtration to give the title compound (91 mg, 31%). NMR: 1.41-1.50 (m, 2H); 1.62-1.78 (m, 2H); 1.82-1.90 (m, 2H); 3.59 (m, 1H); 7.60 (s, 2H); 7.62 (d, 2H); 7.98 (d, 2H); 8.40 (s, 1H); m/z: 345 (MH)+.

Workup

customThe volatiles were removed by evaporation and residue
customwas purified by chromatography on silica gel eluting with ethyl acetate/hexane (50:50)
customThe product was triturated with ether/hexane
filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record: ord-bbd28b5db97945269fde65053f83e457
Source dataset: uspto-grants-2005_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06906065B2

Reaction notes

Loading…