Hydrochloric Acid → HCID 178450823, compound

HRID 2169196Notes

Reaction equation

CO[C:3](=[O:22])/[C:4](/[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[C:5](\O)/[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].Cl.[CH3:24][C:25]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:30])[CH2:26][C:27](=[NH:29])[NH2:28].C[O-].[Na+].Cl>CO.O>[CH2:15]([O:14][C:4]1[C:5]([C:6]([O:8][C:9]([CH3:10])([CH3:11])[CH3:12])=[O:7])=[N:28][C:27]([CH2:26][C:25]([CH3:30])([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:24])=[N:29][C:3]=1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

4-tert-Butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate (4) (652 mg, 2.12 mmol, Eq: 1.5,) and 3-methyl-3-phenylbutanimidamide hydrochloride (54) (300 mg, 1.41 mmol, Eq: 1.00) were stirred in methanol (7.2 ml). The reaction mixture was cooled to 0° C. and sodium methoxide (229 mg, 4.23 mmol, Eq: 3) (powdered, Aldrich) was added. The reaction mixture was stirred at room temperature. The reaction mixture is a suspension. It was stirred overnight. 5 ml 1N aqueous HCl was added and the mixture was diluted with water, filtered through a sintered glass funnel. The solid was washed with water. The solid was placed under high vacuum to dry to give tert-butyl 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylate as a yellow solid (260 mg, 21%) as a 1:1 mixture of tert-butyl 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylate (55) and 3-methyl-3-phenylbutanimidamide. The product was used without further purification.

Workup

stirringIt was stirred overnight
filtrationfiltered through a sintered glass funnel
washThe solid was washed with water
customto dry

Sources & evidence

ORD record: ord-b867189f38284cb59edc004b89209e38
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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