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p-Toluenesulfonic acid → 4-chloro-7-(2,4-dimethoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one

HRID 1685193
Notes
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Reaction equation

HRID 1685193 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][C:16]=2[O:23][CH3:24])[N:5]=[CH:4][N:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[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][C:16]=3[O:23][CH3:24])[C:6]=2[N:5]=[CH:4][N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86641611Methyl 2-(4-chloro-6-(2,4-dimethoxybenzylamino)pyrimidin-5-yl)acetate

Product 1

HCID 569717344-chloro-7-(2,4-dimethoxybenzyl)-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-oneYield 74.05%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
10 °C

Procedure

Combine a solution of methyl 2-(4-chloro-6-(2,4-dimethoxybenzylamino)pyrimidin-5-yl)acetate (1.00 equiv; 2.23 mol; 783 g) in p-toluenesulfonic acid (0.5 equiv; 1.10 mol; 212 g) with Toluene (12 L) and stir at reflux. After 1 h, remove toluene in vacuo and extract with DCM. Wash the organic layer with saturated NaHCO3(aq) and brine, dry over Na2SO4, filter and concentrated in vacuo. Slurry the residue in methanol (2 L) and concentrate in vacuo to approximately 1 L. Cool the slurry to 10° C., filter, wash with cold methanol, and dry to obtain the title compound (1.65 mol; 527 g; 74.05%) as a yellow-orange solid. 1H NMR (400 MHz, CDCl3): 8.59 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 6.43 (d, J=2.0 Hz, 1H), 6.40 (d, J=8.5 Hz, 1H), 4.92 (d, s, 2H), 3.79 (s, 3H), 3.77 (s, 3H), 3.60 (s, 2H).

Workup

  1. temperatureat reflux
  2. customremove toluene in vacuo
  3. extractionextract with DCM
  4. washWash the organic layer with saturated NaHCO3(aq) and brine
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrate in vacuo to approximately 1 L
  9. filtrationfilter
  10. washwash with cold methanol
  11. customdry

Sources & evidence

ORD record
ord-3f63e7b212284b27898a9a6b7465e2b7
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08148387B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes