Sodium Hydroxide → [4-(4-Chloro-7H-Pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl]-methanol

HRID 1295657Notes

Reaction equation

HRID 1295657 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[NH:20][C:14]3[N:15]=[CH:16][N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=2)=[CH:7][CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O.C(OCC)(=O)C>[Cl:19][C:18]1[C:13]2[CH:12]=[C:11]([C:8]3[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=3)[NH:20][C:14]=2[N:15]=[CH:16][N:17]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21225700DiisobutylaluminumhydrideHCID 232826964-(4-Chloro-7H-pyrrolo[2,3-D]pyrimidin-6-YL)benzoic acid ethyl ester

Product 1

HCID 86595337[4-(4-Chloro-7H-Pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl]-methanol

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 30.0 g (100 mmol) 4-(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzoic acid ethyl ester (WO 97/02266) in 450 ml dry THF at 10° C. under N2-atmosphere, 500 ml diisobutyl-aluminium hydride (1 M in THF) were added dropwise. The resulting clear solution is stirred for 1 h and then diluted with 2.1 l of dry THF. Then 98 ml of ethyl acetate are added, followed after 15 min by 45 ml of water and after 1 h by 22.5 ml of 4 N sodium hydroxide. After 1 h stirring, 200 g of Na2SO4 are added and stirring is continued for another hour. The mixture is filtered through Celite (Fluka, Buchs, Switzerland), the residue washed with THF and discarded. Concentration of the filtrate to a volume of ≈0.1 l, addition of 0.3 l of dichloromethane and filtration yields the title compound; Analysis for C13H10ClN3O: calc. C 60.13%, H, 3.88%, N, 16.18%, Cl 13.65%; found C, 60.23%, H 4.03%, N 16.51%, Cl 13.28%.

Workup

  1. stirringAfter 1 h stirring
  2. stirringstirring
  3. waitis continued for another hour
  4. filtrationThe mixture is filtered through Celite (Fluka, Buchs, Switzerland)
  5. washthe residue washed with THF
  6. additionConcentration of the filtrate to a volume of ≈0.1 l, addition of 0.3 l of dichloromethane and filtration

Sources & evidence

ORD record
ord-3583eee6bc0740be8d3b2ae827d2ecde
Source dataset
uspto-grants-2007_07
Patent number
US07244729B2

Reaction notes

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