Hydrochloric Acid → 7-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-n-(1,3,3-trimethylindolin-6-yl)pyrido[3,4-d]pyrimidin-4-amine

HRID 971260Notes

Reaction equation

HRID 971260 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH2:17][CH2:16][C:15]3[C:14]([NH:18][C:19]4[CH:27]=[C:26]5[C:22]([C:23]([CH3:29])([CH3:28])[CH2:24][NH:25]5)=[CH:21][CH:20]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.Cl.[C:31]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([N:8]2[CH2:17][CH2:16][C:15]3[C:14]([NH:18][C:19]4[CH:27]=[C:26]5[C:22]([C:23]([CH3:29])([CH3:28])[CH2:24][N:25]5[CH3:31])=[CH:21][CH:20]=4)=[N:13][CH:12]=[N:11][C:10]=3[CH2:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 120041027-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-n-(3,3-dimethylindolin-6-yl)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 120041037-(3-Chloropyridin-2-yl)-5,6,7,8-tetrahydro-n-(1,3,3-trimethylindolin-6-yl)pyrido[3,4-d]pyrimidin-4-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of compound of Example 69 hydrogen chloride (20 mg) in DMF (5 mL) was added K2CO3 (50 mg), followed by MeI (50 μL). The mixture was stirred at room temperature for 2 h, and then treated with water, extracted with EtOAc (50 mL). The organic layer was separated, washed with brine, dried (Na2SO4), and evaporated. The residue was purified by flash chromatography over silica ghel to give a light yellow solid (10 mg).

Workup

  1. extractionextracted with EtOAc (50 mL)
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography over silica ghel

Sources & evidence

ORD record
ord-8af38c3f5dad42db993a610dd6212e26
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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