N-Methylcyclohexylamine → Cyclohexyl-methyl-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

HRID 398226Notes

Reaction equation

HRID 398226 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:17][NH:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>>[CH:19]1([N:18]([CH3:17])[C:2]2[C:3]3[CH:10]=[C:9]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 53767830Cyclohexyl-methyl-(6-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amineYield 10.5%

Procedure

The product from Method E (50 mg/0.218 mmol) was reacted with 0.12 mL of N-methylcyclohexylamine (0.920 mmol) as described in Method B. The reaction mixture was concentrate in vacuo, methanol was added, and the resulting precipitate filtered to provide 7 mg (10%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3) δ: 1.18-1.25 (m, 1H), 1.47-1.66 (m, 4H), 1.75-1.90 (m, 5H), 3.30 (s, 3H), 4.74 (br, 1H), 6.79 (s, 1H), 7.32-7.36 (m, 1H), 7.47-7.51 (m, 2H), 7.77 (d, 2H, J=7.9 Hz), 8.33 (s, 1H). LRMS: 307 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrate in vacuo, methanol
  2. additionwas added
  3. filtrationthe resulting precipitate filtered

Sources & evidence

ORD record
ord-6b7a2925fa224022a4914c01b884d1d1
Source dataset
uspto-grants-2003_08
Patent number
US06610847B2

Reaction notes

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