1-Butanol → 2,6-Dimethyl-4-[4-(2-hydroxyethyl)-1-piperazinyl]-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one

HRID 1253181Notes

Reaction equation

HRID 1253181 reaction equation
Cl[C:2]1[C:7]2[O:8][CH:9]([CH3:13])[C:10](=[O:12])[NH:11][C:6]=2[N:5]=[C:4]([CH3:14])[N:3]=1.O[CH:16]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[CH3:17].C([OH:28])CCC>>[CH3:14][C:4]1[N:3]=[C:2]([N:21]2[CH2:22][CH2:23][N:18]([CH2:16][CH2:17][OH:28])[CH2:19][CH2:20]2)[C:7]2[O:8][CH:9]([CH3:13])[C:10](=[O:12])[NH:11][C:6]=2[N:5]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 36767354-chloro-2,6-dimethyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-oneHCID 177695631-(Piperazin-1-yl)ethan-1-ol

Product 1

HCID 201372972,6-Dimethyl-4-[4-(2-hydroxyethyl)-1-piperazinyl]-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one

Procedure

A mixture containing 0.86 g of 4-chloro-2,6-dimethyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one (Khim. Geterotsikl. Soed. 1972, 1285), 20 ml of n-butanol and 1.04 g of 1-hydroxyethylpiperazine is refluxed for 7 hours, then evaporated. After adding 20 ml of water, the residue is extracted with ethyl acetate. The organic solution is dried and evaporated. After recrystallizing the residue from ethyl acetate, 0.90 g of product is obtained, m.p.: 160°-161° C.

Workup

  1. temperatureis refluxed for 7 hours
  2. customevaporated
  3. additionAfter adding 20 ml of water
  4. extractionthe residue is extracted with ethyl acetate
  5. customThe organic solution is dried
  6. customevaporated
  7. customAfter recrystallizing the residue from ethyl acetate

Sources & evidence

ORD record
ord-e5177b493fd24c0696b670b6dd7caebc
Source dataset
uspto-grants-1988_05
Patent number
US04748175

Reaction notes

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