Acetic Acid → HCID 45262917, compound

5-Hydroxy-1,4,5,6-tetrahydropyrimidine (JOC, 1966, 31, 3838; 1 g, 10 mmol) was dissolved in glacial acetic acid (25 ml) with stirring, and thionylchloride (0.73 ml, 10 mmol) was added dropwise. The resulting solution was refluxed 19 hours, then evaporated to dryness in vacuo. The residue was taken up in water (5 ml), the pH adjusted to 12 (sat. Na2CO3), and extracted with chloroform. The chloroform was dried (MgSO4) and evaporated in vacuo to 440 mg (25%) product as a clear oil identified by 400 MHz nmr. The oil was converted to its HCl salt in anhydrous ethanol with addition of IM HCl in ether. After evaporation of solvents the resulting crude HCl salt was recrystallized from ethanol to yield 128 mg (7%) white crystals, mp 287°-289° C. 400 MHz nmr and ir confirmed product. Calculated: C 40.34, H 6.2, N 15.69; found: C 40.45, H 6.19, N 15.53.

1. temperatureThe resulting solution was refluxed 19 hours
2. customevaporated to dryness in vacuo
3. extractionextracted with chloroform
4. dry with materialThe chloroform was dried (MgSO4)
5. customevaporated in vacuo to 440 mg (25%) product as a clear oil
6. additionThe oil was converted to its HCl salt in anhydrous ethanol with addition of IM HCl in ether
7. customAfter evaporation of solvents the resulting crude HCl salt
8. customwas recrystallized from ethanol

ORD record

ord-38958a1d739e4abfafa20241effc55d6

Source dataset

uspto-grants-1995_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05403845