Ethyl bromoacetate → HCID 58654406, compound

HRID 1170535Notes

Reaction equation

[N:1]1([C:6]2[N:11]=[C:10]([C:12]#N)[CH:9]=[C:8]([CH3:14])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C1C[O:25]CC1>[Zn].CS(O)(=O)=O>[N:1]1([C:6]2[N:11]=[C:10]([C:12](=[O:25])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:9]=[C:8]([CH3:14])[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

Conditions

Temperature: 67 °C

Procedure

Methanesulfonic acid (200 μL, 3.08 mmol) was added dropwise to a suspension of zinc powder (70.4 g, 1.08 mol) in anhydrous THF (228 mL) and the mixture was heated to 67° C. After 1 hour, a solution of 2-(1H-imidazol-1-yl)-6-methylpyrimidine-4-carbonitrile (20.0 g, 108 mmol) in THF (120 mL) was added followed by subsequent dropwise addition of ethyl 2-bromoacetate (90.8 g, 540 mmol) over a period of 1.5 h. The mixture was stirred for an additional 30 minutes at 67° C. then cooled to rt. The inorganic solids were removed by vacuum filtration, washed with THF (200 mL), and the filtrate was brought to pH=1 with 3 M hydrochloric acid (200 mL). The solution was stirred for 30 minutes at rt prior to removal of the solvent under vacuum. Ethyl 3-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-oxopropanoate (14.3 g) was obtained as yellow solid and was used directly in the next step.

Workup

temperaturethen cooled to rt
customThe inorganic solids were removed by vacuum filtration
washwashed with THF (200 mL)
stirringThe solution was stirred for 30 minutes at rt
customto removal of the solvent under vacuum

Sources & evidence

ORD record: ord-70f9f870412a4311806a7d87805ffd0c
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07825256B2

Reaction notes

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