1-Butanol → HCID 11278574, compound

HRID 1863982Notes

Reaction equation

HRID 1863982 reaction equation
ClCC1C=CC(C2C[C:11]3[N:16]=[CH:15][N:14]=[C:13]([N:17]([CH3:19])[CH3:18])[C:12]=3N=2)=CC=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.[NH2:26][C@H:27]([C:39](O)=O)[CH2:28][C:29]1C=C2C(C=CC=C2)=C[CH:30]=1.[CH2:42](O)[CH2:43][CH2:44][CH3:45]>>[N:21]1([CH2:45][C:44]2[CH:30]=[CH:29][C:28]([C:27]3[NH:26][C:11]4[N:16]=[CH:15][N:14]=[C:13]([N:17]([CH3:18])[CH3:19])[C:12]=4[CH:39]=3)=[CH:42][CH:43]=2)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 4

HCID 2631-ButanolHCID 795ImidazoleHCID 1859152-NaphthylalanineHCID 131727794HCID 131727794, compound

Product 1

HCID 11278574HCID 11278574, compound

Procedure

[6-(4-Chlormethyl-phenyl)-7H-pyrrolo[2,3]pyrimidin-4-yl]-dimethylamine (170 mg, 0.59 mmol) is dissolved in n-butanol (7 mL) at room temperature. Imidazole (326 mg, 4.80 mmol) and a catalytic amount of Nal are added and the mixture is heated to reflux for 1.5 h. It is allowed to cool to room temperature again, concentrated in vacuo to give a yellow solid which is purified by flash chromatography (SiO2, ethyl acetate/MeOH 7:3) to give [6-(4-Imidazol-1-ylmethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-dimethylamine as a yellow solid. C18H18N6: M+H=393.0; 1H-NMR (400 MHz, DMSO-d6): 12.11 (s, 1H, NH), 8.11 (s, 1H), 7.86 (d, 2H), 7.77 (s, 1H), 7.31 (d, 2H), 7.21 (s, 1H), 7.13 (s, 1H), 6.91 (s, 1H), 5.20 (s, 2H), 3.32 (s, 6H). m. p.=273-275° C.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1.5 h
  3. concentrationconcentrated in vacuo
  4. customto give a yellow solid which
  5. customis purified by flash chromatography (SiO2, ethyl acetate/MeOH 7:3)

Sources & evidence

ORD record
ord-1ced03fc1c8d417abc33dc03c2ce83e2
Source dataset
uspto-grants-2009_12
Patent number
US07625894B2

Reaction notes

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