Potassium Carbonate → 5-(1,4,5,6-Tetrahydropyrimidin-1-yl)-3-methyl-2-nitro aniline

HRID 970355Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[NH:13]1[CH2:18][CH2:17][CH2:16][N:15]=[CH:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:15]1([C:2]2[CH:3]=[C:4]([CH3:12])[C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=2)[NH2:7])[CH2:16][CH2:17][CH2:18][N:13]=[CH:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a stirred solution of 2.0 g (11.76 mmol) of 5-fluoro-3-methyl-2-nitro-aniline in 10 mL of DMSO was added 1.2 g (14.11 mmol) of 1,4,5,6-tetrahydropyrimidine, and 2.43 g (17.64 mmol) of potassium carbonate, and the mixture was heated at 100° C. for 10 hrs, cooled, diluted with water, and extracted with Ethylacetate containing 5% methanol. The combined organic extract was washed with water, brine and dried (Na2SO4). Evaporation of the solvent furnished the residue, which was chromatographed (20% of 2M ammonia in methanol and dichloromethane) to produce 1.85 g (67%) of the product as red solid. 1H NMR (400 MHz, CD3OD) δ 7.89 (1H, s), 6.53 (1H, d, J=2.57 Hz), 6.44 ((1H, d, J=2.1 Hz), 7.04 (1H, d, J=2.1 Hz), 3.70 (2H, t, J=6.0 Hz), 3.41 (2H, t, J=5.65 Hz, 2.43 (3H, s), 2.05 (2H, m) LCMS (M+H)+ m/z 235 (t=0.78 min).

Workup

temperaturecooled
extractionextracted with Ethylacetate containing 5% methanol
extractionThe combined organic extract
washwas washed with water, brine
dry with materialdried (Na2SO4)
customEvaporation of the solvent
customfurnished the residue, which
customwas chromatographed (20% of 2M ammonia in methanol and dichloromethane)

Sources & evidence

ORD record: ord-55a7211bcc5e4c288ccd00e26e0459cd
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312215B2

Reaction notes

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