Hydrochloric Acid → HCID 19909617, compound

HRID 374086Notes

Reaction equation

HRID 374086 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][C:10](=O)[N:11]([CH2:12][CH3:13])[C:6]=2[N:5]=[C:4]([CH3:15])[N:3]=1.Cl.[OH-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[C:6]=2[N:5]=[C:4]([CH3:15])[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 54504101HCID 54504101, compound

Product 1

HCID 19909617HCID 19909617, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
115 °C

Procedure

A solution of 2.0 g (8.81 mmole) of 4-chloro-6,7-dihydro-8-ethyl-2-methylpyrimido [5,4-b][1,4]oxazin-7-one in 25 ml of tetrahydrofuran was added dropwise to 3.5 ml of cold (0° C.) borane-methyl sulfide complex in tetrahydrofuran. After the completion of the addition, the mixture was heated at its reflux temperature for three hours. The mixture was cooled and 14 ml of 6N hydrochloric acid was slowly added. This mixture was heated for one hour at 115° C., and was then cooled and neutralized with ammonium hydroxide. The mixture was extracted with chloroform, and the organic layer was then dried and evaporated to provide an oil residue which crystallized on cooling. Nuclear magnetic resonance spectral analysis showed the product to be 4-chloro-6,7-dihydro-8-ethyl-2-methylpyrimido [5,4-b][1,4]oxazine.

Workup

  1. additionAfter the completion of the addition
  2. temperaturethe mixture was heated at its
  3. temperaturereflux temperature for three hours
  4. temperatureThe mixture was cooled
  5. temperaturewas then cooled
  6. extractionThe mixture was extracted with chloroform
  7. customthe organic layer was then dried
  8. customevaporated
  9. customto provide an oil residue which
  10. customcrystallized
  11. temperatureon cooling

Sources & evidence

ORD record
ord-80e9d6cbf2134021b754bd6695f2c1c6
Source dataset
uspto-grants-1992_11
Patent number
US05166343

Reaction notes

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