Guanidine → {1-[4-(2-Amino-5-phenyl-pyrimidin-4-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362166Notes

Reaction equation

[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18](=O)[C:19]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:20]N(C)C)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH2:32][C:33]([NH2:35])=[NH:34].CO[Na]>CN(C=O)C.CC(=O)OCC>[C:1]([O:5][C:6](=[O:31])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:20][N:32]=[C:33]([NH2:35])[N:34]=3)=[CH:16][CH:17]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of compound 1 (3 g, 7.2 mmol) and guanidine (2 g, 35 mmol) in DMF (15 mL) was added MeONa (1.8 g, 35 mmol) and the mixture was heated to 100° C. and stirred for 4 h. The solution was cooled to r.t. and diluted with 80 mL of EA. The organic phase was washed with 0.1N HClaq and brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica gel column chromatography to give 2.1 g of 5-1 as a yellow solid.

Workup

temperatureThe solution was cooled to r.t.
washThe organic phase was washed with 0.1N HClaq and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-696a31ff9ca34d578fd78eef1034b599
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691825B2

Reaction notes

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