Water → 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin

HRID 1789866Notes

Reaction equation

HRID 1789866 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]([C:34]1[N:39]=[CH:38][C:37]([C:40](C)(C)[O:41][SiH2]C(C)(C)C)=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:22])([CH3:21])[CH3:20].O>C1COCC1>[C:19]([O:23][C:24]([N:26]([C:34]1[N:39]=[CH:38][C:37]([CH2:40][OH:41])=[CH:36][N:35]=1)[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:25])([CH3:20])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 1317258312-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin

Product 1

HCID 220360932-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidinYield 53.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (15.3 g, 48.6 mmol) was added to a solution of 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-(ter-butyl-dimethyl-silanyloxymethyl)-pyrimidin (10.0 g, 24.3 mmol) in THF (100 mL) and stirred at room temperature overnight. Water was added and the product extracted with chloroform. The organic phase was dried and concentrated under reduced pressure. Flash chromatography (MeOH/CH2Cl2, 2.5:77.5) gave 2-[N,N-bis(tert-butoxycarbonyl)amino]-5-hydroxymethyl-pyrimidin (4.20 g, 53%).

Workup

  1. extractionthe product extracted with chloroform
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-47147d4078fc4d00bf7261458a1d1430
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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