HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzylamine → 3-benzyl-2-isobutylpyrido[3,4-d]pyrimidin-4(3H)-one

HRID 1867458
Notes
Print preview

Reaction equation

HRID 1867458 reaction equation
[CH2:1]([C:5]1O[C:7](=[O:15])[C:8]2[CH:14]=[CH:13][N:12]=[CH:11][C:9]=2[N:10]=1)[CH:2]([CH3:4])[CH3:3].[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(Cl)(Cl)Cl>[CH2:16]([N:23]1[C:7](=[O:15])[C:8]2[CH:14]=[CH:13][N:12]=[CH:11][C:9]=2[N:10]=[C:5]1[CH2:1][CH:2]([CH3:3])[CH3:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 14798Sodium HydroxideHCID 221726032-isobutyl-4H-pyrido[3,4-d][1,3]oxazin-4-one

Product 1

HCID 221725913-benzyl-2-isobutylpyrido[3,4-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-isobutyl-4H-pyrido[3,4-d][1,3]oxazin-4-one (3.0 g, 14.68 mmol) in CHCl3 was added benzylamine (1.73 g, 16.15 mmol) and the reaction was heated to 60° C. After 3 h, the reaction was cooled to room temperature and solvent removed in vacuo. The resulting residue was dissolved in ethylene glycol and sodium hydroxide (0.385 g, 9.62 mmol) was added. The reaction was stirred overnight at 140° C. After cooling to room temperature and extracting with DCM, the organic solution was washed with water. The solution was dried over sodium sulfate and filtered. Concentration of the organic solution provided the title compound as a brown oil. 1H NMR (500 MHz, CDCl3) δ 1.01 (d, J=7 Hz, 6H), 2.33-2.38 (m, 1H), 2.68 (d, J=7 Hz, 2H), 5.43 (s, 2H), 7.16 (d, J=7.5 Hz, 2H), 7.30-7.40 (m, 3H), 8.06 (d, J=5 Hz, 1H), 8.68 (d, J=5 Hz, 1H), 9.13 (s, 1H). MS [M+H] C18H19N3O=294.1.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customsolvent removed in vacuo
  3. dissolutionThe resulting residue was dissolved in ethylene glycol
  4. temperatureAfter cooling to room temperature
  5. extractionextracting with DCM
  6. washthe organic solution was washed with water
  7. dry with materialThe solution was dried over sodium sulfate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-77c210080410451194b517963a707512
Source dataset
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07632839B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes