Dimethylformamide → 1,3-Bis(3-methoxypropyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

HRID 337613Notes

Reaction equation

HRID 337613 reaction equation
[CH:1]([C:3]1[C:4](=[O:10])[NH:5][C:6](=[O:9])[NH:7][CH:8]=1)=[O:2].Br[CH2:12][CH2:13][CH2:14][O:15][CH3:16].[CH2:17]1[CH2:27]CN2C(=NCCC2)C[CH2:18]1.CN([CH:31]=[O:32])C>>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][N:7]1[CH:8]=[C:3]([CH:1]=[O:2])[C:4](=[O:10])[N:5]([CH2:18][CH2:17][CH2:27][O:32][CH3:31])[C:6]1=[O:9]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 3045905-FormyluracilHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 866459191,3-Bis(3-methoxypropyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

Procedure

To a DMF (0.35 M) solution of 5-formyluracil (1 eq.) was added sequentially at 0° C. 1-bromo-3-methoxypropane (2.2 eq.) and DBU (2.2 eq.). The resulting solution was stirred at RT for 72 h. The volatiles were then removed in vacuo. The crude product mixture thus obtained was directly subjected to purification by way of column chromatography (SiO2, EtOAc) to afford the title compound as a yellow oil.

Workup

  1. customThe volatiles were then removed in vacuo
  2. customThe crude product mixture thus obtained
  3. customwas directly subjected to purification by way of column chromatography (SiO2, EtOAc)

Sources & evidence

ORD record
ord-cde0f4ebe46b4a7b8cbb8028d434ae96
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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