Potassium Carbonate → 6-Benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine

HRID 1020008Notes

Reaction equation

HRID 1020008 reaction equation
[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([NH2:17])[N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([NH2:17])[N:14]=[C:15]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[Cl:20])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 143932216-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

Product 1

HCID 497874276-Benzyl-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamineYield 61.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
95 °C

Procedure

6-benzyl-4-chloro-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-2-ylamine (1.92 g., 7 mmoles) and 2-chlorophenylboronic acid (1.09 g., 7 mmoles) were mixed and stirred in a mixture of acetonitrile and water (50:50, 32 mls); anhydrous potassium carbonate (1.93 g., 14 mmoles) was then added to the stirred reaction mixture under nitrogen. Pd(PPh3)4 (0.2 g.) was then added to the reaction mixture which was stirred and heated at 95° C. for 3 hours also under nitrogen. The reaction mixture was then allowed to cool to room temperature and a beige solid formed. This suspension was quenched with water (150 mls) and the solid filtered and washed with water (100 mls) dried in a vacuum desiccator. The product was then eluted through a ‘silica plug’ in ethyl acetate, after evaporation the solid was slurried in ether to give, after filtering and drying a white solid (1.5 g., 61.2% yield). LC-MS (retention 2.65 mins, mass 351 M+H).

Workup

  1. temperatureto cool to room temperature
  2. customa beige solid formed
  3. customThis suspension was quenched with water (150 mls)
  4. filtrationthe solid filtered
  5. washwashed with water (100 mls)
  6. customdried in a vacuum desiccator
  7. washThe product was then eluted through a ‘silica plug’ in ethyl acetate
  8. customafter evaporation the solid
  9. customto give
  10. filtrationafter filtering
  11. customdrying a white solid (1.5 g., 61.2% yield)
  12. customLC-MS (retention 2.65 mins, mass 351 M+H)

Sources & evidence

ORD record
ord-a4842633536f48f795580456c4b2ddd4
Source dataset
uspto-grants-2014_05
Patent number
US08716302B2

Reaction notes

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