Water → 2-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-ol

HRID 82146Notes

Reaction equation

HRID 82146 reaction equation
[BH4-].[Li+].[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[C:14](OC)=[O:15])[CH:5]=1.O>C(O)C>[I:3][C:4]1[C:12]2[CH:11]=[N:10][CH:9]=[N:8][C:7]=2[N:6]([C:13]([CH3:19])([CH3:18])[CH2:14][OH:15])[CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 70817219HCID 70817219, compound

Product 1

HCID 708175262-(5-Iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Lithium borohydride (32.3 mL, 64.6 mmol, 2.0 M in THF) was added to methyl 2-(5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-methylpropanoate (8.92 g, 25.9 mmol) (see Preparation 21) in ethanol (70 mL). The mixture was stirred at room temperature for 17 hours then water (70 mL) was added. The mixture was evaporated in vacuo then the residue was partitioned between DCM (250 mL) and water (50 mL). The aqueous phase was extracted with DCM:MeOH (90:10, 2×250 mL) and the combined organic phases were dried over magnesium sulfate and evaporated in vacuo to afford the title compound as an off-white solid in 100% yield, 8.20 g.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between DCM (250 mL) and water (50 mL)
  3. extractionThe aqueous phase was extracted with DCM:MeOH (90:10, 2×250 mL)
  4. dry with materialthe combined organic phases were dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-74a5983e4f464f568c56ec53293c3908
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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