Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → 2-(benzyloxymethyl)-4-hydroxy-N-(naphthalen-2-ylmethyl)pyrimidine-5-carboxamide

HRID 574670Notes

Reaction equation

HRID 574670 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([C:17]([OH:19])=O)=[CH:12][N:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=N[C:30]2[CH:31]=[CH:32][CH:33]=[N:34][C:29]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH2:1]([O:8][CH2:9][C:10]1[N:15]=[C:14]([OH:16])[C:13]([C:17]([NH:34][CH2:33][C:32]2[CH:5]=[CH:4][C:3]3[C:30](=[CH:29][CH:6]=[CH:7][CH:2]=3)[CH:31]=2)=[O:19])=[CH:12][N:11]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524758HCID 178524758, compound

Product 1

HCID 1785227702-(benzyloxymethyl)-4-hydroxy-N-(naphthalen-2-ylmethyl)pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of compound 2-e (5 g, 19.2 mmol) in DMF (50 mL) was added HATU (8.04 g, 21.1 mmol) and EIPEA (2.73 g, 21.1 mmol). The reaction mixture was stirred at ambient temperature until all dissolved. To this stirred solution was added compound 2-22-a (3.17 g, 20.2 mmol) in DMF (20 mL) via syringe. The solution was stirred at room temperature overnight. The reaction mixture was poured into ice-water and extracted with DCM and then concentrated to give a residue. The residue was purified by column chromatography with the eluent DCM:MeOH=60:1 to afford product, 2-22-b, (5.2 g, 68%). 1H NMR (300 MHz, CDCl3): δ 9.38 (s, 1H), 8.90 (s, 1H), 7.81-7.75 (m, 4H), 7.43-7.34 (m, 8H), 4.77 (d, J=6.0 Hz, 2H), 4.67 (s, 2H), 4.56 (s, 2H). LC-MS: (M+H)+ 400.

Workup

  1. stirringThe solution was stirred at room temperature overnight
  2. extractionextracted with DCM
  3. concentrationconcentrated
  4. customto give a residue
  5. customThe residue was purified by column chromatography with the eluent DCM
  6. customMeOH=60:1 to afford product, 2-22-b, (5.2 g, 68%)

Sources & evidence

ORD record
ord-8cc2cfe4ad9440b2b874aed8e6f91e6b
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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