Guanidine Hydrochloride → 4'-Methyl-2-methylsulfanyl-[4,5']bipyrimidinyl-2'-ylamine

HRID 1397165Notes

Reaction equation

CN(C)[CH:3]=[C:4]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)[C:5](=O)[CH3:6].C([O-])([O-])=O.[K+].[K+].Cl.[NH2:24][C:25]([NH2:27])=[NH:26]>CN(C=O)C>[CH3:6][C:5]1[C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=2)=[CH:3][N:24]=[C:25]([NH2:27])[N:26]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 4-Dimethylamino-3-(2-methylsulfanyl-pyrimidin-4-yl)-but-3-en-2-one (18) (1.02 g, 4.30 mmol) in DMF (14 mL) was added K2CO3 (1.782 g, 12.89 mmol) and Guanidine HCl (0.616 g, 6.45 mmol) and the resulting suspension was stirred at 120° C. for 1 hour. The DMF was evaporated and the crude residue partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, and concentrated. The crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM to give the desired product as a light yellow solid (800 mg, 80%). MS (ES+): m/z=234.3/235.4 (100/20) [MH+]. HPLC: tR=1.01 minutes over 3 minutes. Purity: 70% [HPLC (LC/MS) at 220 nm].

Workup

customThe DMF was evaporated
customthe crude residue partitioned between water and ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried with sodium sulfate
concentrationconcentrated
customThe crude residue was purified by flash chromatography with a gradient of 1-12% MeOH in DCM

Sources & evidence

ORD record: ord-025e070e01ca447cbb1ff1508aaefbdb
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901147B2

Reaction notes

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