5-Bromouracil → 5-morpholinopyrimidine-2,4(1H,3H)-dione

HRID 1486530Notes

Reaction equation

HRID 1486530 reaction equation
Br[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1>>[O:13]1[CH2:14][CH2:15][N:10]([C:2]2[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=2)[CH2:11][CH2:12]1

Participants

3

Reactant 2

HCID 58025-BromouracilHCID 8083Morpholine

Product 1

HCID 6877025-morpholinopyrimidine-2,4(1H,3H)-dioneYield 76%

Procedure

The title compound was obtained according to the procedure described for the synthesis of Example 10 (Step1), starting from 5-bromouracil (0.10 g, 052 mmol) and 20 equivalents of morpholine. The crude was purified by precipitation in acidic water (10 mL, pH 5) to afford the title compound (0.08 g, 76%) as white, powder. 1H NMR (400 MHz, DMSO-d6): δ 2.74-2.84 (m, 4H), 3.64 (t, J=4.6 Hz, 4H), 6.72 (s, 1H), 10.47 (s, 1H), 11.05 (s, 1H).

Workup

  1. customdescribed for the synthesis of Example 10 (Step1)
  2. customThe crude was purified by precipitation in acidic water (10 mL, pH 5)

Sources & evidence

ORD record
ord-2b5546c8874643589e7805d438fb11bd
Source dataset
uspto-grants-2016_08
Patent number
US09428465B2

Reaction notes

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