Ammonium Chloride → Thieno[2,3-d]pyrimidine-6-carbaldehyde

HRID 32518Notes

Reaction equation

HRID 32518 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CON(C)[C:10]([C:12]1[S:20][C:15]2[N:16]=[CH:17][N:18]=[CH:19][C:14]=2[CH:13]=1)=[O:11].[Cl-].[NH4+]>C1COCC1>[N:16]1[C:15]2[S:20][C:12]([CH:10]=[O:11])=[CH:13][C:14]=2[CH:19]=[N:18][CH:17]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 85929707N-Methoxy-N-methylthieno[2,3-d]pyrimidine-6-carboxamide2×

Product 1

HCID 17965793Thieno[2,3-d]pyrimidine-6-carbaldehydeYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

LiAlH4 (1M in THF, 0.26 mL) was added dropwise to N-methoxy-N-methylthieno[2,3-d]pyrimidine-6-carboxamide (intermediate 12) (117 mg) in THF (6 mL) at −78° C. under an inert atmosphere. The reaction was allowed to stir at −78° C. for 30 minutes and then allowed to warm to 0° C. Saturated aqueous-ammonium chloride (2 mL) was added and allowed to stir at 0° C. for 10 minutes. The organic layer was separated and the aqueous layer extracted with diethyl ether (2×15 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with hexane:EtOAc (1:4) afforded the title compound as a white solid (60 mg, 70%);

Workup

  1. temperatureto warm to 0° C
  2. stirringto stir at 0° C. for 10 minutes
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with diethyl ether (2×15 mL)
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification by flash chromatography on silica eluting with hexane:EtOAc (1:4)

Sources & evidence

ORD record
ord-042e87916871493aaa72026bd7b28e9c
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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