Potassium Carbonate → HCID 89995977, compound

HRID 1480780Notes

Reaction equation

HRID 1480780 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=4)=[CH:15][C:14]=3[O:25][CH3:26])[N:10]=[CH:11][C:6]=2[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH:33]1([SH:39])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>CN(C=O)C>[CH:33]1([S:39][C:2]2[C:7]3[N:8]=[C:9]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([C:19]5[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=5)=[CH:15][C:14]=4[O:25][CH3:26])[N:10]=[CH:11][C:6]=3[CH:5]=[CH:4][N:3]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 15290CyclohexanethiolHCID 89995981HCID 89995981, compound

Product 1

HCID 89995977HCID 89995977, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-N-(2-methoxy-4-(1-methyl-1H-pyrazol-4-yl)phenyl)pyrido[3,4-d]pyrimidin-2-amine (Example 94, 26 mg, 0.071 mmol) and potassium carbonate (15 mg, 0.109 mmol) in DMF (0.35 mL) was treated with cyclohexanethiol (12 μL, 0.098 mmol) and stirred at room temperature for 4 days. An additional batch of potassium carbonate (10 mg, 0.07 mmol) and thiol (12 μL, 0.098 mmol) were added and the mixture stirred at 50° C. for 18 hours. The reaction was quenched with brine and extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated. The residue was purified by silica gel column chromatography eluting with 0 to 80% EtOAc in cyclohexane to give the title compound (30 mg, 94%).

Workup

  1. stirringthe mixture stirred at 50° C. for 18 hours
  2. customThe reaction was quenched with brine
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with 0 to 80% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-1e27c110b05d410bbed984fa3b76a987
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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