Sodium borohydride → HCID 136018754, compound

HRID 2054373Notes

Reaction equation

HRID 2054373 reaction equation
[CH3:1][N:2]1[C:10](S(C)(=O)=O)=[N:9][C:8]2[C:7](=[O:15])[NH:6][C:5]3=[CH:16][C:17]([O:19][CH2:20][CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:18][N:4]3[C:3]1=2.[BH4-].[Na+]>CN1C(=O)N(C)CCC1>[CH3:1][N:2]1[CH:10]=[N:9][C:8]2[C:7](=[O:15])[NH:6][C:5]3=[CH:16][C:17]([O:19][CH2:20][CH2:21][O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:18][N:4]3[C:3]1=2

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 136018758HCID 136018758, compound

Product 1

HCID 136018754HCID 136018754, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

A mixture of Example 84 Part B (1.8575 g, 4.60 mmol) and NiBr2(DME) (142 mg, 0.46 mmol) in DMPU (100 mL) was treated with NaBH4 (697 mg, 18.4 mmol) under stirring at room temperature. After 20 h, there was still significant amount of starting material left, therefore more NaBH4 (500 mg, 13.2 mmol) and NiBr2(DME) (1.44 g, 4.67 mmol) were added. Over the subsequent 24 h, additional NaBH4 (2.0 g, 53 mmol) and NiBr2(DME) (2.7 g, 8.75 mmol) were added to push the reaction to completion. The mixture was then quenched carefully with MeOH at ice temperature and filtered. The filtrate was neutralized with 1.0 N HCl to PH=7.0, precipitating some sticky solid. The solution layer was separated and concentrated. The residual solution was precipitated with EtOAc/hexanes to remove DMPU. The precipitated solid was purified by flash chromatography (MeOH/CHCl3, 3%), giving the title compound (658 mg, 44% yield). ESI m/z=326.25 [(M+H)+; calcd for C16H15N5O3+H: 326.13].

Workup

  1. waitleft
  2. customthe reaction to completion
  3. customThe mixture was then quenched carefully with MeOH at ice temperature
  4. filtrationfiltered
  5. customprecipitating some sticky solid
  6. customThe solution layer was separated
  7. concentrationconcentrated
  8. customThe residual solution was precipitated with EtOAc/hexanes
  9. customto remove DMPU
  10. customThe precipitated solid was purified by flash chromatography (MeOH/CHCl3, 3%)

Sources & evidence

ORD record
ord-e3be9beaf2724fbcb3e6f69fd3bb2afe
Source dataset
uspto-grants-2008_02
Patent number
US07329668B2

Reaction notes

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