Formaldehyde → HCID 178482566, compound

HRID 2373517Notes

Reaction equation

HRID 2373517 reaction equation
F[C:2](F)(F)C(O)=O.N[C:9]1([C:15]2[N:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[S:32]([CH3:35])(=[O:34])=[O:33])=[O:22])[C:18]([OH:36])=[C:17]([OH:37])[N:16]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1.C(N(CC)CC)C.C([O-])(=O)C.[Na+].C=O.[C:52]([BH3-])#[N:53].[Na+].FC(F)(F)C(O)=O>CO>[CH3:2][N:53]([CH3:52])[C:9]1([C:15]2[N:20]=[C:19]([C:21]([NH:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=3[S:32]([CH3:35])(=[O:34])=[O:33])=[O:22])[C:18]([OH:36])=[C:17]([OH:37])[N:16]=2)[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1

Participants

8

Reactant 6

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydride2×HCID 178504815HCID 178504815, compound

Product 1

HCID 178482566HCID 178482566, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4-aminotetrahydro-2H-pyran-4-yl)-N-[4-fluoro-2-(methylsulfonyl)benzyl]-5,6-dihydroxypyrimidine-4-carboxamide trifluoroacetate (C-32) in MeOH was treated with triethylamine (1 eq.), sodium acetate (1.6 eq.), formaldehyde 37% w/w aq. soln. (3 eq.), and sodium cyanoborohydride (1.43 eq.). The mixture was left stirring at room temperature for 1 h. Trifluoroacetic acid (3 eq) and sodium cyanoborohydride (0.5 eq) were added, left stirring overnight. The reaction mixture was concentrated and the title compound (C-33) as trifluoro acetate salt was obtained by preparative HPLC purification (C18, eluting with water and acetonitrile containing 0.1% trifluoroacetic acid in gradient).

Workup

  1. waitThe mixture was left
  2. waitleft
  3. stirringstirring overnight
  4. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a7cfd95e56d640d788f816eb6028f80c
Source dataset
uspto-grants-2008_12
Patent number
US07459452B2

Reaction notes

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