Hydrochloric Acid → 4-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

HRID 1685192Notes

Reaction equation

HRID 1685192 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9](OC)=[O:10])=[C:6]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[N:5]=[CH:4][N:3]=1.Cl.O>>[Cl:1][C:2]1[C:7]2[CH2:8][C:9](=[O:10])[N:13]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:6]=2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86641609Methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate

Product 1

HCID 866416104-Chloro-7-(4-methoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-oneYield 76.4%

Conditions

Temperature
100 °C

Procedure

Add a solution of methyl 2-(4-chloro-6-(4-methoxybenzylamino)pyrimidin-5-yl)acetate (16.21 g, 1.00 equiv; 50.38 mmol) to HCl (4M in dioxane) (126 mL; 10 equiv; 503.79 mmol) and water (4.54 mL; 5 equiv; 251.89 mmol) and stir at 100° C. for 2 h. Remove dioxane in vacuo and extract with EA. Wash the organic layer with saturated NaHCO3, water, then brine. Dry over MgSO4, filter and concentrate in vacuo. Purify the residue by ISCO 330 g using EA:hex 20 to 70% as eluent to obtain the title compound (11.15 g; 38.49 mmol; 76.39%) as a yellow solid. 1H NMR (300 MHz, DMSO): 8.65 (s, 1H), 7.29-7.26 (m, 2H), 6.89-6.85 (m, 2H), 4.79 (s, 2H), 3.80 (s, 2H), 3.71 (s, 3H).

Workup

  1. extractionRemove dioxane in vacuo and extract with EA
  2. washWash the organic layer with saturated NaHCO3, water
  3. dry with materialDry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customPurify the residue by ISCO 330 g

Sources & evidence

ORD record
ord-6715b2f750b8489ca30caccf4e1c4ad4
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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