Isopropanol → HCID 58316829, compound

HRID 1187280Notes

Reaction equation

HRID 1187280 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C)C.[CH3:15][CH:16]([NH2:18])[CH3:17]>O>[CH:16]([NH:18][C:2]1[C:3]2[CH:10]=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1)([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6363Isopropylamine2×HCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Product 1

HCID 58316829HCID 58316829, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (1, 168 mg, 1.09 mmol), 2.00 mL of isopropyl alcohol is added, followed by 2-propanamine (11, 0.280 mL, 3.28 mmol). The reaction is heated by microwave at 120° C. for 20 minutes, then an additional 40 minutes. Another 0.250 mL of 2-propanamine is added and heated at 120° C. for 60 minutes. The reaction is poured into water and extracted with ethyl acetate. The organic layer is concentrated under vacuum and purified by silica gel column chromatography, eluting with a gradient of 1-5% methanol in dichloromethane. Appropriate fractions are combined and concentrated under vacuum to provide the desired compound (12, 172 mg). MS (ESI) [M+H+]+=176.85.

Workup

  1. customan additional 40 minutes
  2. temperatureheated at 120° C. for 60 minutes
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer is concentrated under vacuum
  5. custompurified by silica gel column chromatography
  6. washeluting with a gradient of 1-5% methanol in dichloromethane
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-45858edc874b4e7aa05e59cf5dcec08e
Source dataset
uspto-grants-2014_03
Patent number
US08673928B2

Reaction notes

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