Water → [2-(Thiophen-2-yl)pyrimidin-5-yl]methanol

HRID 2062126Notes

Reaction equation

HRID 2062126 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)=[N:9][CH:10]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[S:12]1[CH:13]=[CH:14][CH:15]=[C:11]1[C:8]1[N:9]=[CH:10][C:5]([CH2:3][OH:2])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 12044630HCID 12044630, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 24229731[2-(Thiophen-2-yl)pyrimidin-5-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

0.175 g of 2-thiophen-2-yl-pyrimidine-5-carboxylic acid methyl ester was dissolved in 3 mL of tetrahydrofuran. The reaction was cooled to 0° C. (ice-water bath) and then 2.39 mL of diisobutylaluminumhydride (1.0 M in tetrahydrofuran) were added dropwise. The reaction was left stirring at 0° C. for 30 minutes, then at room temperature overnight. Water was added, the mixture was extracted with ethylacetate, and the organic layer was dried with magnesium sulphate, filtered and concentrated to afford the crude (2-thiophen-2-yl-pyrimidin-5-yl)-methanol, which was used without purification for the next reactions.

Workup

  1. waitThe reaction was left
  2. customat room temperature
  3. customovernight
  4. extractionthe mixture was extracted with ethylacetate
  5. dry with materialthe organic layer was dried with magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b533af8a252248368e91383f6d99fd9d
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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