Ethyl 2-bromopropionate → 2,6-Dimethyl-8-(1-ethoxycarbonyl-1-ethyl)-4-(4-morpholinyl)-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one

HRID 1253192Notes

Reaction equation

HRID 1253192 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.Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>>[CH3:14][C:4]1[N:3]=[C:2]([N:11]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)[C:7]2[O:8][CH:9]([CH3:13])[C:10](=[O:12])[N:11]([CH:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH3:22])[C:6]=2[N:5]=1

Participants

3

Reactant 2

HCID 79040Ethyl 2-bromopropionateHCID 36767354-chloro-2,6-dimethyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one

Product 1

HCID 704169272,6-Dimethyl-8-(1-ethoxycarbonyl-1-ethyl)-4-(4-morpholinyl)-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-oneYield 42%

Procedure

Starting from 4-chloro-2,6-dimethyl-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one (Khim. Geterotsikl. Soed. 1972, 1285) and ethyl 2-bromopropionate, Example 32 is followed. After refluxing for 12 hours and evaporating, the residue [the most part of which is 4-chloro-2,6-dimethyl-(1-ethoxycarbonyl-1-ethyl)-6,7-dihydro-8H-pyrimido[5,4-b][1,4]oxazin-7-one] is reacted with morpholine and worked up as described in Example 1, except that the evaporation residue is triturated with ether, filtered, the filtrate is evaporated and the residue is recrystallized from n-hexane to give the product in a yield of 42%, m.p.: 80°-82° C.

Workup

  1. temperatureAfter refluxing for 12 hours
  2. customevaporating
  3. customis reacted with morpholine
  4. customis triturated with ether
  5. filtrationfiltered
  6. customthe filtrate is evaporated
  7. customthe residue is recrystallized from n-hexane
  8. customto give the product in a yield of 42%, m.p.: 80°-82° C.

Sources & evidence

ORD record
ord-8b28d5b9e71d4dd08e66c0db70be88ef
Source dataset
uspto-grants-1988_05
Patent number
US04748175

Reaction notes

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