Water → 5-Bromo-2-(methylthio)pyrimidine-4-carbaldehyde

HRID 2170319Notes

Reaction equation

HRID 2170319 reaction equation
[Br:1][C:2]1[C:3]([C:10](N(OC)C)=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[C:3]([CH:10]=[O:11])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 902803345-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide

Product 1

HCID 542714955-Bromo-2-(methylthio)pyrimidine-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-bromo-N-methoxy-N-methyl-2-(methylthio)pyrimidine-4-carboxamide (11A, 8.2 g, 28 mmol) in THF (120 mL) was added dropwise to a suspension of lithium aluminum hydride (1.06 G, 28 mmol) and THF (120 mL) at −78° C. The mixture was stirred for 10 minutes after addition finish. H2O (1.06 mL), 15% aqueous NaOH solution (1.06 mL) and H2O (3.18 mL) were successively added to the mixture at 0° C. very slowly. The resulting precipitate was filtered and washed with THF. The filtrate was concentrated in vacuo to afford crude of the title compound. MS (m/z): 233.14, [M+H]+.

Workup

  1. additionafter addition finish
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with THF
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-56e05154f5b4483a8c1a60f055d18f8e
Source dataset
uspto-grants-2015_06
Patent number
US09050344B2

Reaction notes

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