Acetic Acid → 2-(1-hydroxyethyl)pyrimidin-4(3H)-one

HRID 586205Notes

Reaction equation

HRID 586205 reaction equation
[Na].O[CH:3]=[CH:4][C:5]([O:7]CC)=O.Cl.[OH:11][CH:12]([CH3:16])[C:13]([NH2:15])=[NH:14].C(O)(=O)C>O>[OH:11][CH:12]([C:13]1[NH:15][C:5](=[O:7])[CH:4]=[CH:3][N:14]=1)[CH3:16]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 223286992-Hydroxypropanimidamide hydrochlorideHCID 24196931Ethyl 3-hydroxy-acrylate sodium salt

Product 1

HCID 110189492-(1-hydroxyethyl)pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a solution of ethyl 3-hydroxy-acrylate sodium salt (prepared according to the method of Preparation Twelve, Step C, 1301 g, 9.42 mol) in water (1.3 L) was added a solution of 2-hydroxy-propionamidine hydrochloride (prepared according to the method of Preparation Twelve, Step B, 610 g, 4.9 mol) in water (1.3 L) at ambient temperature and stirred, for 48 h. The solution was adjusted to pH 7.0 with acetic acid then continuously extracted with chloroform for 48 h. The extract was dried over sodium sulfate and filtered. The filtrate was concentrated to a solid, slurried in ethyl ether, filtered, and dried to give the title compound as a solid, 232 g (38%). mp: 121-124° C.; 1H NMR (DMSO-d6, 400 MHz) δ 1.30 (d, 3H), 4.46 (q, 1H), 5.62 (br s, 1H), 6.13 (d, 1H), 7.80 (d, 1H).

Workup

  1. customprepared
  2. extractionthen continuously extracted with chloroform for 48 h
  3. dry with materialThe extract was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to a solid, slurried in ethyl ether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-9cb6e11dc5424aa88056233a5b24613f
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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