Diisobutylaluminumhydride → HCID 59732398, compound

HRID 131197Notes

Reaction equation

HRID 131197 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[S:20][CH:19]=[CH:18][C:8]=2[N:9]=[C:10]([CH2:12][C:13](OCC)=[O:14])[N:11]=1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[S:20][CH:19]=[CH:18][C:8]=2[N:9]=[C:10]([CH2:12][CH2:13][OH:14])[N:11]=1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 59732331HCID 59732331, compound

Product 1

HCID 59732398HCID 59732398, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 4-(2-furyl)thieno[3,2-d]pyrimidine-2-acetate (0.10 g, 0.35 mmol) in dichloromethane (13 mL) at −75° C. was treated dropwise with di-iso-butylaluminium hydride (0.87 mL, 1.0-M), stirred for 17 h, warmed to ambient temperature and partitioned between Rochelle's salt and dichloromethane. The combined organic phase was dried (MgSO4), concentrated in vacuo and purified by chromatography (SiO2:EtOAc) to give the title compound (21 mg, 25%) as a white solid.

Workup

  1. custompartitioned between Rochelle's salt and dichloromethane
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by chromatography (SiO2:EtOAc)

Sources & evidence

ORD record
ord-0bc87771c6124cc78f870331c5ffc4d4
Source dataset
uspto-grants-2008_06
Patent number
US07384949B2

Reaction notes

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