Hydrochloric Acid → HCID 178450868, compound

HRID 2169206Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[NH:12])[NH2:11].C[O:14][C:15](=O)/[C:16](/[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[C:17](\O)/[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].C[O-].[Na+].Cl>CO>[C:21]([O:20][C:18]([C:17]1[NH:12][C:10]([CH2:9][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[Br:2])=[N:11][C:15](=[O:14])[C:16]=1[O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:19])([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-Bromophenyl)acetimidamide hydrochloride (2 g, 8.01 mmol, Eq: 1.00) and 4-tert-butyl 1-methyl 2-(benzyloxy)-3-hydroxyfumarate (4) (3.44 g, 11.2 mmol, Eq: 1.39) were dissolved in methanol (40.0 ml) and cooled down to 0° C. At that temperature sodium methoxide (1.37 g, 24.0 mmol, Eq: 3) was added. After another 15 minutes at this temperature, the resulting suspension was allowed to warm to room temperature overnight. A little methanol (˜5 ml) was added and the yellow suspension was cooled to 0° C. 1M HCl (˜50 ml) was added and a precipitate formed. The suspension was stirred for −20 minutes. The solid was collected by filtration, washed with water and a little methanol/water 9/1 and dried to afford 5-(benzyloxy)-2-(2-bromobenzyl)-6-oxo-3,6-dihydro-pyrimidine-4-carboxylic acid tert-butyl ester (2.69 g, 5.71 mmol, 71.2% yield) (67) as an off-white solid.

Workup

temperatureto warm to room temperature overnight
temperaturethe yellow suspension was cooled to 0° C
customa precipitate formed
filtrationThe solid was collected by filtration
washwashed with water
dry with materiala little methanol/water 9/1 and dried

Sources & evidence

ORD record: ord-3e390ceac728411e9a7abd89bd68f901
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045486B2

Reaction notes

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