2-(Dimethylamino)ethanol → 2-(Dimethylamino)ethyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetate

HRID 1617193Notes

Reaction equation

HRID 1617193 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[NH2:19][C:20]1[N:25]=[C:24]([CH3:26])[C:23]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([CH2:34][C:35]([OH:37])=[O:36])=[CH:30][CH:29]=2)=[C:22]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[N:21]=1.[CH3:44][N:45]([CH3:49])[CH2:46][CH2:47]O>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:19][C:20]1[N:25]=[C:24]([CH3:26])[C:23]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([CH2:34][C:35]([O:37][CH2:47][CH2:46][N:45]([CH3:49])[CH3:44])=[O:36])=[CH:32][CH:33]=2)=[C:22]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[N:21]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 111923Propylphosphonic anhydrideHCID 595906372-(4-((2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetic acid

Product 1

HCID 578248262-(Dimethylamino)ethyl 2-(4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)phenyl)acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of T3P (1.57M in THF, 0.42 ml) was added to a mixture of the product from example 34 step (viii) (0.15 g), N,N-dimethylethanolamine (0.08 ml), TEA (0.3 ml) and DMAP (0.02 g) in DMF (5 ml) and stirred at rt for 24 h. The mixture was partitioned between DCM/water, the organics separated, washed with aq NaHCO3 soln, brine, dried and evaporated under reduced pressure. The residue was purified by RPHPLC, then the product dissolved in MeCN (10 ml) and PS-TBD (0.1 g) added and left for 2 h. The mixture was filtered, the solvent evaporated under reduced pressure and the residue triturated with isohexane and filtered to afford the title compound, 0.034 g.

Workup

  1. customThe mixture was partitioned between DCM/water
  2. washthe organics separated, washed with aq NaHCO3 soln
  3. dry with materialbrine, dried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by RPHPLC
  6. dissolutionthe product dissolved in MeCN (10 ml)
  7. additionPS-TBD (0.1 g) added
  8. waitleft for 2 h
  9. filtrationThe mixture was filtered
  10. customthe solvent evaporated under reduced pressure
  11. customthe residue triturated with isohexane
  12. filtrationfiltered

Sources & evidence

ORD record
ord-038bfd84ae524b07b931ea669369c56f
Source dataset
uspto-grants-2014_07
Patent number
US08765939B2

Reaction notes

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