Benzhydrylamine → N-benzhydryl-2-(benzyloxymethyl)-4-hydroxypyrimidine-5-carboxamide

HRID 574661Notes

Reaction equation

HRID 574661 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.[C:20]1([CH:26]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[NH2:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:26]([NH:27][C:17]([C:13]1[C:14]([OH:16])=[N:15][C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:11][CH:12]=1)=[O:19])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524758HCID 178524758, compound2×

Product 1

HCID 178522799N-benzhydryl-2-(benzyloxymethyl)-4-hydroxypyrimidine-5-carboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of step D product (2-e) (20.0 g, 76.9 mmol), diphenylmethanamine (15.5 g, 84.6 mmol), HATU (43.8 g, 115.0 mmol), and TEA (23.3 g, 230 mmol) in DMF (100 mL) were combined and stirred at the ambient temperature overnight. Ice-water (40 mL) was added to the reaction mixture and extracted with DCM (30 mL×2). The organic phase was concentrated to give a residue, which was purified by silica gel chromatography (eluented with PE/EA=3:1˜1:1) to a afford the product, 2-f, (31.0 g, 96%). 1H NMR (300 MHz, CD3OD): δ4.29 (s, 2H), 4.52 (s, 2H), 6.22 (s, 1H), 7.21-7.23 (m, 15H), 8.60 (s, 1H). LC-MS: (M+H)+ 426.

Workup

  1. extractionextracted with DCM (30 mL×2)
  2. concentrationThe organic phase was concentrated
  3. customto give a residue, which
  4. customwas purified by silica gel chromatography (eluented with PE/EA=3:1˜1:1) to

Sources & evidence

ORD record
ord-555c526e44b54b298cc6ab70cfc83765
Source dataset
uspto-grants-2015_05
Patent number
US09034851B2

Reaction notes

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