Methylamine → HCID 178482337, compound

HRID 1880018Notes

Reaction equation

HRID 1880018 reaction equation
ClC(Cl)C.[Br:5][C:6]1[CH:15]=[N:14][C:13]2[NH:12][C:11](=O)[C:10]([CH3:18])([CH3:17])[O:9][C:8]=2[CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:25][NH2:26]>C(Cl)Cl>[Br:5][C:6]1[CH:15]=[N:14][C:13]2[NH:12]/[C:11](=[N:26]/[CH3:25])/[C:10]([CH3:18])([CH3:17])[O:9][C:8]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 63651,1-DichloroethaneHCID 24819Phosphorus pentachlorideHCID 577420407-bromo-2,2-dimethyl-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

Product 1

HCID 178482337HCID 178482337, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A dichloroethane (5 mL) solution of 7-bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (520 mg, 2 mmol) and phosphorus pentachloride (840 mg, 4 mmol) was irradiated in a microwave oven for 10 min at 160° C. The solution was cooled to −78° C. and methylamine (2M in THF) was added it slowly until it became permanently basic. The mixture was diluted with CH2Cl2, washed with dilute solution of NaOH, dried and evaporated. Crystallization from CH2Cl2/hexane afforded 480 mg (89%) of the title compound. 1H NMR (300 MHz, CDCl3, 8) 8.07 (d, J=2.1 Hz, 1H), 7.21 (d, J=2.1 Hz, 1H), 4.9 (s, br, 1H), 3.06 (d, J=4.5 Hz, 3H), 1.46 (s, 6H). MS (ESI) m/e 270 (M+H)+.

Workup

  1. washwashed with dilute solution of NaOH
  2. customdried
  3. customevaporated
  4. customCrystallization from CH2Cl2/hexane

Sources & evidence

ORD record
ord-6dedc78406a24bae9e0980b675a5871e
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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