4-Methylmorpholine → HCID 67014569, compound

HRID 1158775Notes

Reaction equation

HRID 1158775 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]([C:15]([OH:17])=O)=[CH:5][N:4]=1.[CH3:19][NH:20][CH2:21][C@H:22]([OH:30])[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1.Cl.CN1CCOCC1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>O1CCCC1>[OH:30][CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([OH:29])[CH:24]=1)[CH2:21][N:20]([CH3:19])[C:15]([C:6]1[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[N:8][C:3]([N:2]([CH3:1])[CH3:18])=[N:4][CH:5]=1)=[O:17]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 5284443Phenylephrine HydrochlorideHCID 10490410HCID 10490410, compound

Product 1

HCID 67014569HCID 67014569, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Dimethylamino-4-phenylpyrimidine-5-carboxylic acid (1.22 g, 5 mmol) is dissolved in tetrahydrofuran (60 ml). After 5 minutes of stirring to the solution are added: L-phenylephrine hydrochloride (1.22 g, 6 mmol) in tetrahydrofuran (50 ml), after another 5 minutes of stirring the N-methylmorpholine (1.21 g, 12 mmol) and after 2 minutes of stirring the 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (1.66 g, 6 mmol). The reaction mixture is stirred for 2 hours at room temperature, then heated at reflux temperature for 2 hours. The solvent is removed in vacuum. To the residue water (50 ml) is added, and the mixture is extracted with chloroform (75 ml), the extract is washed with 10% sodium carbonate solution (35 ml), with water (35 ml), dried over sodium sulphate and evaporated. The residue is chromatographed on silicagel using chloroform-methanol 100/1-100/5 mixture eluent. 0.36 g of the title compound is obtained, m.p.: 79-81° C.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 2 hours at room temperature
  3. temperatureheated
  4. temperatureat reflux temperature for 2 hours
  5. customThe solvent is removed in vacuum
  6. additionTo the residue water (50 ml) is added
  7. extractionthe mixture is extracted with chloroform (75 ml)
  8. washthe extract is washed with 10% sodium carbonate solution (35 ml), with water (35 ml)
  9. dry with materialdried over sodium sulphate
  10. customevaporated
  11. customThe residue is chromatographed on silicagel

Sources & evidence

ORD record
ord-eb4f4ea8e2a549fd989d745a3e04734a
Source dataset
uspto-grants-2010_10
Patent number
US07812031B2

Reaction notes

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