Potassium Carbonate → HCID 90402730, compound

HRID 2200609Notes

Reaction equation

[NH2:1][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[NH:5][C:4](=[O:10])[CH:3]=1.CO[CH:13](OC)[N:14]([CH3:16])[CH3:15].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:5]2[C:4](=[O:10])[CH:3]=[C:2](/[N:1]=[CH:16]/[N:14]([CH3:13])[CH3:15])[N:7]([CH3:8])[C:6]2=[O:9])=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 6-amino-1-methylpyrimidine-2,4(1H,3H)-dione (13.1 g, 92.9 mmol) in DMF (200 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (13 mL, 97.9 mmol) and the mixture was stirred at 40° C. for 3 h. Then 1-(chloromethyl)-4-methoxybenzene (15.05 mL, 111.5 mmol) was added followed by potassium carbonate (25.64 g, 0.186 mmol) and DMF (100 mL), the resulting mixture was stirred at 80° C. for 48 h. The reaction was cooled and diluted with ethyl acetate. The organic phase was washed with brine, dried and concentrated to give a crude product which was purified by silica gel chromatography eluting with methanol/DCM (1:80 to 1:20) to give (E)-N′-(1-(4-methoxybenzyl)-3-methyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-N,N-dimethylformimidamide (7.8 g, 26.5% yield) as yellow solid. LCMS retention time 1.023 min; LCMS MH+ 317.

Workup

stirringthe resulting mixture was stirred at 80° C. for 48 h
temperatureThe reaction was cooled
washThe organic phase was washed with brine
customdried
concentrationconcentrated
customto give a crude product which
customwas purified by silica gel chromatography
washeluting with methanol/DCM (1:80 to 1:20)

Sources & evidence

ORD record: ord-68fbb4119ae042c48bac7ebefcfc4b36
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359359B2

Reaction notes

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