3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester → 4-(3-methyl-1,6-diazaspiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1912386Notes

Reaction equation

HRID 1912386 reaction equation
C(OC([N:11]1[C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:15]2)[CH:13]([CH3:29])[CH2:12]1)=O)C1C=CC=CC=1>CO.O1CCCC1.[C].[Pd]>[CH3:29][CH:13]1[C:14]2([CH2:19][CH2:18][CH2:17][N:16]([C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:15]2)[NH:11][CH2:12]1

Participants

4

Reactant 1

HCID 582932883-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester

Product 1

HCID 582933114-(3-methyl-1,6-diazaspiro[3.5]non-6-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 93.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of an optically-active compound of 3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.5]nonane-1-carboxylic acid benzyl ester (2.84 g) in methanol/tetrahydrofuran (14 ml/14 ml) was added 10% palladium carbon (568 mg), and the mixture was hydrogenated under 4 atmospheres. The mixture was filtered through Celite, and the filtrate was concentrated under reduced pressure. The resulting residue was slurry-washed with toluene/tetrahydrofuran (95/5, 9 ml) to give the titled compound (1.74 g).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe resulting residue was slurry-washed with toluene/tetrahydrofuran (95/5, 9 ml)

Sources & evidence

ORD record
ord-7f8425f26ee6460ebcd2bb40010b14a9
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

Loading…