Pyridine → 7-cyclopentyl-2-(5-hydroxymethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile

HRID 1483058Notes

Reaction equation

HRID 1483058 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[N:16]=[CH:17][C:18]3[CH:23]=[C:22]([C:24]#[N:25])[N:21]([CH:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[C:19]=3[N:20]=2)=[N:12][CH:13]=1)(C)(C)C.N1C=CC=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[CH:26]1([N:21]2[C:19]3[N:20]=[C:15]([NH:14][C:11]4[CH:10]=[CH:9][C:8]([CH2:7][OH:6])=[CH:13][N:12]=4)[N:16]=[CH:17][C:18]=3[CH:23]=[C:22]2[C:24]#[N:25])[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 3

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 178455434HCID 178455434, compound

Product 1

HCID 583154307-cyclopentyl-2-(5-hydroxymethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrileYield 53%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamino]-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile in THF (2.0 mL) is added HF.pyridine (0.080 mL) at 0° C. The reaction mixture stirred at room temperature for 16 h before it is diluted with ethyl acetate, ished with saturated NaHCO3 solution, dried (MgSO4), filtered and concentrated. Trituration with diethyl ether gave 7-cyclopentyl-2-(5-hydroxymethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carbonitrile, 68 mg, 53% yield (over 2 steps). MS (ESI) m/z 335.0 (M+H)+ (method A).

Workup

  1. customat 0° C
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b5f5a2c918f645ec9faa10736d705bb5
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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