Sodium Bicarbonate → HCID 86615713, compound

HRID 216257Notes

Reaction equation

HRID 216257 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[CH3:11][N:12]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH:14]([CH2:22][NH2:23])[CH2:13]1.C([O-])(O)=O.[Na+]>CCO>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH3:10])[N:3]=[C:2]([NH:23][CH2:22][CH:14]2[CH2:13][N:12]([CH3:11])[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[O:15]2)[CH:7]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidineHCID 155503741-(4-Methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanamine

Product 1

HCID 86615713HCID 86615713, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4,6-dichloro-2-methoxy-pyrimidine (0.27 g, 1.48 mmol), C-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-methylamine (0.22 g, 1.23 mmol), and NaHCO3 (0.62 g, 7.4 mmol) in EtOH (7 mL) is heated to reflux for 5 h. The mixture is concentrated in vacuo. The residue is partitioned between EtOAc and water, and extracted with EtOAc. The extracts are dried (Na2SO4), and concentrated to afford (6-chloro-2-methoxy-pyrimidin-4-yl)-(4-methyl-3,4-dihydro-2H-benzo[1,4]oxazin-2-ylmethyl)-amine (0.39 g). LCMS: RT=3.27 minutes; MS: 321 (M+H).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 5 h
  3. concentrationThe mixture is concentrated in vacuo
  4. customThe residue is partitioned between EtOAc and water
  5. extractionextracted with EtOAc
  6. dry with materialThe extracts are dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b4afbf1142274a78bfc41712b95a8161
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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