Butyric Acid → HCID 59834585, compound

HRID 271605Notes

Reaction equation

HRID 271605 reaction equation
[NH2:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[N:17]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:10]3[N:11]=[C:12]([C:15]#[N:16])[N:13]=[CH:14][C:9]=3[CH:8]=2)=[CH:4][CH:3]=1.[C:25](O)(=[O:29])[CH2:26][CH2:27][CH3:28].CCN=C=NCCCN(C)C.Cl.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C>[C:15]([C:12]1[N:13]=[CH:14][C:9]2[CH:8]=[C:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:25](=[O:29])[CH2:26][CH2:27][CH3:28])=[CH:24][CH:23]=3)[N:17]([CH2:18][C:19]([CH3:21])([CH3:20])[CH3:22])[C:10]=2[N:11]=1)#[N:16]

Participants

6

Reactant 4

HCID 264Butyric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59834697HCID 59834697, compound

Product 1

HCID 59834585HCID 59834585, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-(4-amino-benzyl)-7-(2,2-dimethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-2-carbonitrile (0.3 mmol) in DMF (4 ml), butyric acid (0.36 mmol), water soluble carbodiimide (0.45 mmol) and 1-hydroxybenzotriazole hydrate (0.45 mmol) are added at 0° C. and then the reaction mixture is stirred at room temperature for 1 day. The reaction mixture is quenched with ammonium chloride and extracted with AcOEt. The organic layer is washed with brine, dried over sodium sulfate and evaporated in vacuo to give 129 mg of crude product. Purification of the residue by silica gel column chromatography affords the title compound in 96% yield. Rf=0.46 (n-hexane:AcOEt=1:1)

Workup

  1. customThe reaction mixture is quenched with ammonium chloride
  2. extractionextracted with AcOEt
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customto give 129 mg of crude product
  7. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-95ffa8f065bf43f1ab523aba5481b57c
Source dataset
uspto-grants-2008_11
Patent number
US07452886B2

Reaction notes

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