Tetrahydrofurfuryl alcohol → 5-Fluoro-2-[(oxolan-2-yl)methoxy]pyrimidin-4(3H)-one

HRID 372678Notes

Reaction equation

HRID 372678 reaction equation
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[H-].[Na+].Cl[C:11]1[NH:16][C:15](=[O:17])[C:14]([F:18])=[CH:13][N:12]=1>C1(C)C=CC=CC=1>[CH2:1]([O:7][C:11]1[NH:16][C:15](=[O:17])[C:14]([F:18])=[CH:13][N:12]=1)[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7360Tetrahydrofurfuryl alcoholHCID 24758Sodium hydrideHCID 2553942-Chloro-5-fluoropyrimidin-4(3H)-one

Product 1

HCID 127836795-Fluoro-2-[(oxolan-2-yl)methoxy]pyrimidin-4(3H)-oneYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 40 g quantity of tetrahydrofurfuryl alcohol and 7.2 g of sodium hydride are added to 200 ml of absolute toluene, and the mixture is stirred at 75°-80° C for 15 hours. Subsequently 14.9 g of 2-chloro-5-fluoropyrimidin-4-one is added to the reaction mixture, and the resulting mixture is heated in a sealed tube at 148° to 150° C for 5 hours for reaction. The resulting reaction mixture is treated in the same manner as in Example 6 to give 15.4 g of white crystalline 2-tetrahydrofurfuryloxy-5-fluoropyrimidin-4-one in a yield of 72.0%, m.p. 89°-91° C.

Workup

  1. temperaturethe resulting mixture is heated in a sealed tube at 148° to 150° C for 5 hours for reaction
  2. customThe resulting reaction mixture
  3. additionis treated in the same manner as in Example 6

Sources & evidence

ORD record
ord-422dfea120514d258b576d25b18b6389
Source dataset
uspto-grants-1978_05
Patent number
US04092313

Reaction notes

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