1-(3,3-Dimethoxy-propyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione → 3-[5-(2,4-Dimethyl-oxazol-5-yl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-propionaldehyde

HRID 12693Notes

Reaction equation

C[O:2][CH:3](OC)[CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([C:12]2[O:16][C:15]([CH3:17])=[N:14][C:13]=2[CH3:18])[C:9](=[O:19])[NH:8][C:7]1=[O:20]>C1COCC1>[CH3:17][C:15]1[O:16][C:12]([C:10]2[C:9](=[O:19])[NH:8][C:7](=[O:20])[N:6]([CH2:5][CH2:4][CH:3]=[O:2])[CH:11]=2)=[C:13]([CH3:18])[N:14]=1

Participants

Conditions

Temperature: 45 °C

Procedure

1-(3,3-Dimethoxy-propyl)-5-(2,4-dimethyl-oxazol-5-yl)-1H-pyrimidine-2,4-dione (Prep63, 150 mg, 0.49 mmol) was dissolved in THF (10 mL) and 1N HClaq (3 mL) was added. The mixture was stirred at 45° C. for 1 hour. After cooling and neutralization with a saturated solution of NaHCO3 the product was extracted with DCM. The organic phase was dried (Na2SO4) and evaporated to give 74 mg of the title compound (58% yield).

Workup

addition1N HClaq (3 mL) was added
temperatureAfter cooling
extractionneutralization with a saturated solution of NaHCO3 the product was extracted with DCM
dry with materialThe organic phase was dried (Na2SO4)
customevaporated

Sources & evidence

ORD record: ord-32bf4fdbe827430eb8603188e5851cc8
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727988B2

Reaction notes

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