Ethyl formate → HCID 178517896, compound

HRID 329585Notes

Reaction equation

HRID 329585 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([O:12]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](OCC)=O.[H-].[Na+].S(O)(O)(=O)=O.[N:27]1([C:33](=[NH:35])[NH2:34])[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[C:10]([OH:12])=[N:35][C:33]([N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[N:34][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 290299Ethyl 2-(benzyloxy)acetateHCID 12427953Sulfuric acid--morpholine-4-carboximidamide (1/1)

Product 1

HCID 178517896HCID 178517896, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 4-alkoxy-2-morpholino-5-pyrimidinols (D represents alkoxy) can be prepared by reacting a 1:1 mixture of ethyl benzyloxyacetate and ethyl formate with sodium hydride in toluene and the product is then reacted with 4-morpholinecarboximidamide sulfate to give 5-benzyloxy-2-morpholino-4-pyrimidinol. The latter compound is converted to 5-benzyloxy-4-chloro-2-morpholinopyrimidine by reaction with phosphorus oxychloride. The ring chlorine is then replaced by an alkoxy group with an alkali alkoxide to give 4-alkoxy-5-benzyloxy-2-morpholinopyrimidine. The benzyloxy group is then converted to the OH group by hydrogenation in the presence of a solvent and a hydrogenation catalyst.

Sources & evidence

ORD record
ord-62ae6666699b4bb79835ca1c0763c163
Source dataset
uspto-grants-1990_01
Patent number
US04892732

Reaction notes

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