Diisopropylethylamine → HCID 118073689, compound

HRID 928160Notes

Reaction equation

HRID 928160 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4](Cl)[N:3]=1.[NH2:15][C:16]1[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=1.CCN(C(C)C)C(C)C>C(O)CCC.C(OCC)(=O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]([CH3:13])[CH3:12])=[C:4]([NH:15][C:16]2[CH:17]=[N:18][N:19]([CH3:21])[CH:20]=2)[N:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 47709901-methyl-1H-pyrazol-4-amineHCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine

Product 1

HCID 118073689HCID 118073689, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
100 °C

Procedure

2,6-Dichloro-9-isopropyl-9H-purine (1.16 g, 5 mmol), as prepared in step 1 of Example 1, was mixed with 4-amino-1-methylpyrazole (1.02 g, 10 mmol) and DIPEA (1.74 mL, 10 mmol) in nBuOH (33 mL) and was stirred and heated at 100° C. (block temperature) for 1 hr. The reaction was cooled, and the volatiles were removed under vacuum to give a dark residue. Ethyl acetate (120 mL) was added and the mixture was washed with sat. aq. NaHCO3 (3×30 mL), dried over Na2SO4 and evaporated to give a dark residue. This residue was dissolved in ethyl acetate, passed through a thin pad of silica gel, and eluted with 90% ethyl acetate-10% ammonia (7 N in methanol). The eluent was evaporated to afford the title compound as a dark solid (1.43 g, 98% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 10.41 (br. s., 1 H) 8.38 (s, 1 H) 8.00 (s, 1 H) 7.68 (s, 1 H) 4.71 (quin, J=6.72 Hz, 1 H) 3.84 (s, 3 H) 1.52 (d, J=6.72 Hz, 6 H). m/z (APCI+) for C12H14ClN7 292.1 with Cl isotope pattern (M+H)+.

Workup

  1. temperatureThe reaction was cooled
  2. customthe volatiles were removed under vacuum
  3. customto give a dark residue
  4. washthe mixture was washed with sat. aq. NaHCO3 (3×30 mL)
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give a dark residue
  8. washeluted with 90% ethyl acetate-10% ammonia (7 N in methanol)
  9. customThe eluent was evaporated

Sources & evidence

ORD record
ord-550eb649ece3488caceec650ca7444e1
Source dataset
uspto-grants-2016_03
Patent number
US09290496B2

Reaction notes

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