Carbonic acid-guanidine (1:1) → 2-amino-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3H-pyrimidin-4-one

HRID 81765Notes

Reaction equation

C[O-].[Na+].C(=O)(O)O.[NH2:8][C:9]([NH2:11])=[NH:10].C([O:14][C:15](=O)[C:16]([O:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([O:28][CH3:29])=[CH:23][C:22]=1[CH:30]([CH3:32])[CH3:31])=[CH:17]OC)C>CS(C)=O>[NH2:10][C:9]1[NH:11][C:15](=[O:14])[C:16]([O:20][C:21]2[CH:26]=[C:25]([CH3:27])[C:24]([O:28][CH3:29])=[CH:23][C:22]=2[CH:30]([CH3:32])[CH3:31])=[CH:17][N:8]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of NaOMe [prepared from sodium (0.05 g, 2.17 mmol) in anhydrous methanol (5 ml)], was added guanidine carbonate. After 5 minutes, a solution of 2-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3-methoxy-acrylic acid ethyl ester (0.22 g, 0.713 mmol) in anhydrous DMSO (10 ml) was added. The mixture was heated at 120° C. for 3 hours and was cooled and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of drying agent, the organic solution was concentrated under reduced pressure. The residue was purified with silica gel chromatography (5% methanol in methylene chloride/0.1% concentrated NH4OH) to yield 2-amino-5-(2-isopropyl-4-methoxy-5-methyl-phenoxy)-3H-pyrimidin-4-one as pale yellow solid (0.045 g, 22%). MS M+H=290.

Workup

temperaturewas cooled
custompartitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried over anhydrous sodium sulfate
customAfter removal
customof drying agent
concentrationthe organic solution was concentrated under reduced pressure
customThe residue was purified with silica gel chromatography (5% methanol in methylene chloride/0.1% concentrated NH4OH)

Sources & evidence

ORD record: ord-7d0b7c5cfb0d440c9ccb0d78ad386dec
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846705B2

Reaction notes

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