Neopentylamine → 2-(methylthio)-N-neopentylpyrido[3,4-d]pyrimidin-8-amine

HRID 1480810Notes

Reaction equation

HRID 1480810 reaction equation
Cl[C:2]1[C:7]2[N:8]=[C:9]([S:12][CH3:13])[N:10]=[CH:11][C:6]=2[CH:5]=[CH:4][N:3]=1.[CH2:14]([NH2:19])[C:15]([CH3:18])([CH3:17])[CH3:16]>CN1C(=O)CCC1.C([O-])(O)=O.[Na+].CCOC(C)=O>[CH3:13][S:12][C:9]1[N:10]=[CH:11][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=2[N:8]=1

Participants

6

Reactant 2

HCID 79882NeopentylamineHCID 899960258-Chloro-2-(methylthio)pyrido[3,4-d]pyrimidine

Product 1

HCID 899962902-(methylthio)-N-neopentylpyrido[3,4-d]pyrimidin-8-amineYield 74%

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 8-chloro-2-(methylthio)pyrido[3,4-d]pyrimidine (Preparation 33, 1 g, 4.72 mmol) in NMP (15 mL) was added neopentylamine (5.5 mL, 4.72 mmol). The reaction mixture was heated to 80° C. for 20 hours. The reaction mixture was diluted with saturated aqueous NaHCO3 (50 mL) and EtOAc (2×50 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 0-100% EtOAc in cyclohexane give the title compound (915 mg, 74%).

Workup

  1. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by silica gel column chromatography
  5. washeluting with 0-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-432899b054b24bf98e41f426e166f12f
Source dataset
uspto-grants-2016_08
Patent number
US09409907B2

Reaction notes

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