Tetrahydrofuran → HCID 58299662, compound

HRID 875991Notes

Reaction equation

HRID 875991 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([C:13]3[C:14](OC)=[N:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=3)=[CH:11][N:10]=[C:9]([NH2:23])[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1>N1C=CC=CC=1>[CH:1]1([N:6]2[C:7]3[N:8]=[C:9]([NH2:23])[N:10]=[CH:11][C:12]=3[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[N:15][C:14]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724254Sodium bis(trimethylsilyl)amideHCID 67234124N4-Cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine

Product 1

HCID 58299662HCID 58299662, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

A 10 mL reaction vessel was charged with N4-cyclopentyl-5-(2,6-dimethoxypyridin-3-yl)pyrimidine-2,4-diamine (267) (50.0 mg, 159 μmol) dissolved in dry pyridine (1 mL) under argon. Sodium bis(trimethylsilyl)amide in THF (1.0M, 0.349 mL, 349 μmol) was added and the reaction heated with microwave energy (300 W) for 12 minutes at 150° C. The solvent was removed in vacuo. Silica gel chromatography of the residue (gradient elution dichloromethane/0-5% methanol) afforded compound 268 as an off-white solid (28 mg, 62%)

Workup

  1. customA 10 mL reaction vessel
  2. customThe solvent was removed in vacuo
  3. washSilica gel chromatography of the residue (gradient elution dichloromethane/0-5% methanol)

Sources & evidence

ORD record
ord-59a6dc38036f451f879f45a4eadcfe0e
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Reaction notes

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