1,2,3,6-Tetrahydropyridine → 2-methoxyethyl 2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidinecarbamate

HRID 27232

Reaction equation

HRID 27232 reaction equation
[NH2:1][C:2]1[N+:7]([O-])=[C:6]([NH:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])[CH:5]=[C:4](Cl)[N:3]=1.[NH:18]1[CH2:23][CH2:22][CH:21]=[CH:20][CH2:19]1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH:9][C:10]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[O:11])[CH:5]=[C:4]([N:18]2[CH2:19][CH:20]=[CH:21][CH2:22][CH2:23]2)[N:3]=1

Participants

4

Reactant 2

HCID 127501,2,3,6-TetrahydropyridineHCID 178496340HCID 178496340, compound

Product 1

HCID 202857752-methoxyethyl 2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidinecarbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
45 °C

Procedure

2.5 G. of 2-methoxyethyl 2-amino-6-chloro-4-pyrimidinecarbamate-3-oxide are mixed under argon with 3 ml. of 1,2,5,6-tetrahydropyridine and 25 ml. of chloroform. The mixture is stirred at 45° C. for 12 hours, then cooled and washed with 15 ml. of water. The product is extracted with chloroform, the organic phase is dried over sodium sulfate and the solvent is distilled off under reduced pressure. The residue obtained is crystallized from methylene chloride/ether, there being obtained pure 2-methoxyethyl 2-amino-6-[3,6-dihydro-1(2H)-pyridyl]-4-pyrimidinecarbamate having a melting point of 136° C.

Workup

  1. temperaturecooled
  2. washwashed with 15 ml
  3. extractionThe product is extracted with chloroform
  4. dry with materialthe organic phase is dried over sodium sulfate
  5. distillationthe solvent is distilled off under reduced pressure
  6. customThe residue obtained
  7. customis crystallized from methylene chloride/ether, there

Sources & evidence

ORD record
ord-0b729c248c43465bb70369dea04a29fa
Source dataset
uspto-grants-1980_09
Patent number
US04220772

Linked notes

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