Ethanol → HCID 178469751, compound

HRID 1005977Notes

Reaction equation

HRID 1005977 reaction equation
C([O-])C.[Na+].C(O)C.Cl.[N:9]1[CH:14]=[CH:13][CH:12]=[N:11][C:10]=1[C:15]([NH2:17])=[NH:16].C(O[CH:21]=[C:22]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25]CC)=O)C>O>[CH2:31]([O:30][C:28]([C:22]1[C:23]([OH:25])=[N:16][C:15]([C:10]2[N:11]=[CH:12][CH:13]=[CH:14][N:9]=2)=[N:17][CH:21]=1)=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 702EthanolHCID 6871Diethyl (ethoxymethylene)malonateHCID 2723922Sodium ethoxideHCID 219837312-Amidinopyrimidine hydrochloride

Product 1

HCID 178469751HCID 178469751, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a fresh prepared solution of sodiumethanolate in ethanol (prepared from 0.44 g (18.92 mmol) Na in 20 ml Ethanol) 1.50 g (9.46 mmol) pyrimidine-2-carboxamidine hydrochloride was added. After 10 min. 1.89 ml (9.46 mmol) diethyl ethoxymethylenemalonate was added at 0° and the resulting suspension was stirred for 12 hrs. After addition of 20 ml H2O, the pH was adjusted to 5 and the aqueous phase was extracted three times with CH2Cl2. The combined organic phases were dried (Na2SO4), filtered and evaporated. The residue was triturated with 5 ml diisopropylether, filtered off and dried to give 1.62 g (70%) 4-hydroxy-[2,2′]bipyrimidinyl-5-carboxylic acid ethyl ester as a light yellow powder, MS (EI): 246.1 (M+).

Workup

  1. extractionthe aqueous phase was extracted three times with CH2Cl2
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was triturated with 5 ml diisopropylether
  6. filtrationfiltered off
  7. customdried

Sources & evidence

ORD record
ord-15de80f9103e4b009b658fe2b8e40d0c
Source dataset
uspto-grants-2004_09
Patent number
US06787539B2

Reaction notes

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