Pyridine → N1-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2-phenylacetamide

HRID 251497Notes

Reaction equation

HRID 251497 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][C:3]=1[O:23][CH3:24].N1C=CC=CC=1.[C:31]1([CH2:37][C:38](Cl)=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C1(CS(Cl)(=O)=O)C=CC=CC=1>ClCCl>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][C:38](=[O:39])[CH2:37][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:3]([O:23][CH3:24])[CH:4]=3)=[CH:9][N:10]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 74740Phenylmethanesulfonyl chlorideHCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 58089297N1-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2-phenylacetamideYield 18.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (28 mg, 0.086 mmol) was dissolved in dichloromethane (1 mL). Pyridine (1 mL) was added followed by 2-phenylethanoyl chloride (14 uL, 0.105 mmol). After stirring overnight, another 14 uL of phenylmethanesulfonyl chloride was added and the reaction mixture was stirred overnight. The solvent was removed and the residue was purified by preparative thin layer chromatogram eluted with dichlormethane/methanol (95:5) to give N1-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]-2-phenylacetamide (7 mg, 0.0158 mmol). 1H NMR (DMSO-d6) δ 1.89 (m, 6H), 2.25 (m, 2H), 3.77 (s, 3H), 3.79 (s, 2H), 5.21 (m, 1H), 5.56 (bs, 2H), 6.89 (s, 1H), 6.99 (s, 1H), 7.05 (d, J=8.22, 1H), 7.36 (m, 5H), 7.81 (s, 1H), 8.27 (s, 1H), 8.43 (d, J=8.23 Hz, 1H). LC/MS MH+=442.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customThe solvent was removed
  3. customthe residue was purified by preparative thin layer chromatogram
  4. washeluted with dichlormethane/methanol (95:5)

Sources & evidence

ORD record
ord-ed3543d024ad4bd78df1e45d183e518d
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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