2,4-Dichloro-6-morpholino-1,3,5-triazine → HCID 57968244, compound

HRID 1665508Notes

Reaction equation

HRID 1665508 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.C([Sn](CCCC)(CCCC)[CH:20]1[CH2:25][CH2:24][CH:23]=[CH:22][O:21]1)CCC>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:6]1[N:7]=[C:2]([C:24]2[CH2:23][CH2:22][O:21][CH2:20][CH:25]=2)[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:5]=1

Participants

5

Reactant 2

HCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 13836887HCID 13836887, compound

Product 1

HCID 57968244HCID 57968244, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In a three necked flask under nitrogen equipped was dissolved 2,4-dichloro-6-morpholin-4-yl-[1,3,5]triazine (610 mg, 2.6 mmol), tributyldihydropyranylstannane (1.45 g, 3.89 mmol, 1.5 eq), and (Ph3P)2PdCl2 (150 mg, 0.21 mmol, 0.1 eq) in anhydrous dioxan (5 ml). The reaction mixture was heated under stirring to 90° C. for 16 hrs. For purification silica gel (10 g) was added to the mixture and the solvent was removed to let the product adsorbed on the silica gel. The silica gel plug was placed on a column and the mixture was flash chromatographed with hexane:ethyl acetate (10:1) to give after removal solvent the product as off white solid (345 mg=47% yield); MS (ESI) m/z 281.

Workup

  1. customIn a three necked flask under nitrogen equipped
  2. temperatureThe reaction mixture was heated
  3. customFor purification silica gel (10 g)
  4. additionwas added to the mixture
  5. customthe solvent was removed
  6. customchromatographed with hexane:ethyl acetate (10:1)
  7. customto give
  8. customafter removal solvent the product as off white solid (345 mg=47% yield)

Sources & evidence

ORD record
ord-a0b40328059648a99642bfc322a45e95
Source dataset
uspto-grants-2011_10
Patent number
US08039469B2

Reaction notes

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