Sodium hydride → HCID 178494685, compound

HRID 329584Notes

Reaction equation

HRID 329584 reaction equation
C[C:2]1[C:7]([OH:8])=C[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C[O:16][CH2:17][C:18]([O:20][CH3:21])=O.[H-].[Na+].S(O)(O)(=O)=O.N1(C(=N)N)CCOC[CH2:30]1>C1(C)C=CC=CC=1>[CH3:21][O:20][C:18]1[C:17]([OH:16])=[N:5][C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[N:3][C:2]=1[CH2:7][O:8][CH3:30]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 80507Methyl methoxyacetateHCID 12427953Sulfuric acid--morpholine-4-carboximidamide (1/1)HCID 19871031HCID 19871031, compound

Product 1

HCID 178494685HCID 178494685, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The 4-methyl-2-morpholino-5-pyrimidinol (D represents methyl) can be prepared by reacting methyl methoxyacetate with sodium hydride in toluene and the product is then reacted with 4-morpholinecarboximidamide sulfate to give 5-methoxy-6-methoxymethyl-2-morpholino-4-pyrimidinol. This latter compound is converted to 4-chloro-5-methoxy-6-methoxymethyl-2-morpholinopyrimidine by reaction with phosphorus oxychloride. The ring chlorine and the methoxy group in the methoxymethyl group are replaced with hydrogen on reduction with zinc in 1 normal NaOH and reaction with sodium ethylmercaptide in dimethylformamide then yields the desired pyrimidinol.

Sources & evidence

ORD record
ord-bb97353796044e548c0a59b5a162605b
Source dataset
uspto-grants-1990_01
Patent number
US04892732

Reaction notes

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