Methanol → HCID 86300750, compound

HRID 1024663Notes

Reaction equation

HRID 1024663 reaction equation
[CH3:1][O:2][C:3]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[CH:45][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]4[C@@H:18]([CH2:26][N:27]([CH:42]([CH3:44])[CH3:43])[CH2:28][CH2:29][CH2:30][N:31]4C(=O)C5C(=CC=CC=5)C4=O)[O:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1.CO>CN>[CH3:1][O:2][C:3]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[CH:45][C:4]=1[CH2:5][NH:6][C:7]1[C:8]2[CH:15]=[CH:14][N:13]([C@H:16]3[C@@H:20]4[O:21][C:22]([CH3:24])([CH3:25])[O:23][C@@H:19]4[C@@H:18]([CH2:26][N:27]([CH:42]([CH3:44])[CH3:43])[CH2:28][CH2:29][CH2:30][NH2:31])[O:17]3)[C:9]=2[N:10]=[CH:11][N:12]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 67817151HCID 67817151, compound

Product 1

HCID 86300750HCID 86300750, compound

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent

Procedure

2-(3-((((3aR,4R,6R,6aR)-6-(4-((2,4-dimethoxybenzyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl)(isopropyl)amino)-propyl)isoindoline-1,3-dione (1.37 g, 2.00 mmol) was dissolved in 2M methylamine in methanol (30 mL, 60 mmol). The solution was stirred at room temperature for 5 minutes then heated at 55-60° C. After 1 h, the SM was consumed by HPLC. The reaction mixture was cooled to room temperature and concentrated in vacuo. The resultant tan oil was taken up in 20 mL MeOH and concentrated. The procedure was repeated to an oil. The material was placed on high vacuum to yield a solid which contained the title compound along with N-methylphthalimide and was used as is in the next step: MS (ESI+) for C29H42N6O5 m/z 555.4 (M+H)+; HPLC ret. time 2.57 min.

Workup

  1. temperaturethen heated at 55-60° C
  2. waitAfter 1 h
  3. customthe SM was consumed by HPLC
  4. temperatureThe reaction mixture was cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. concentrationconcentrated
  7. customto yield a solid which

Sources & evidence

ORD record
ord-944a103b70114f23881042e896efc486
Source dataset
uspto-grants-2014_05
Patent number
US08722877B2

Reaction notes

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