Hydrochloric Acid → 2-[6-oxopyrimidin-1(6H)-yl]propanoic acid

HRID 1888176Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4](=[O:7])[NH:3][CH:2]=1.[OH-].[Na+].Br[C@H:11]([CH3:15])[C:12]([OH:14])=[O:13].Cl>>[O:7]=[C:4]1[N:3]([CH:11]([CH3:15])[C:12]([OH:14])=[O:13])[CH:2]=[N:1][CH:6]=[CH:5]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 14798Sodium Hydroxide

HCID 206954-Hydroxypyrimidine

HCID 6992152(2R)-2-Bromopropanoic acid

Product 1

HCID 579074812-[6-oxopyrimidin-1(6H)-yl]propanoic acid

Conditions

Temperature: 85 °C

Procedure

To pyrimidin-4(3H)-one (0.908 g, 9.45 mmol) was added a 5 N sodium hydroxide solution (3.8 ml) followed by (2R)-2-bromopropanoic acid (0.95 ml, 11 mmol). The reaction mixture was heated at 85° C. for 1 h. After cooling to ambient temperature the reaction was neutralized with 2 N hydrochloric acid (5.2 ml) and then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in aeetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white solid. 1H NMR (DMSO-d6) δ: 8.48 (d, J=2.7 Hz, 1H), 7.88 (dd, J=7.8, 2.8 Hz, 1H), 6.12 (d, J=7.6 Hz, 1H), 5.04 (q, J=7.3 Hz, 1H), 1.64 (d, J=7.5 Hz, 3H). LC/MS 169.1 (M+1)+.

Workup

temperatureAfter cooling to ambient temperature the reaction
customdirectly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in aeetonitrile/0.1% trifluoroacetic acid in water gradient)
customRemoval of the volatiles in vacuo

Sources & evidence

ORD record: ord-58ac3fba3b4d4e06ad01a47d7df8aa23
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501786B2

Reaction notes

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