Diisopropylethylamine → HCID 178454119, compound

HRID 577681Notes

Reaction equation

HRID 577681 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=2[N:7]=1.[C:20]([O:24][C:25](=[O:32])[NH:26][C@H:27]1[CH2:30][C@H:29]([NH2:31])[CH2:28]1)([CH3:23])([CH3:22])[CH3:21].CCN(C(C)C)C(C)C>CC(O)C>[C:20]([O:24][C:25](=[O:32])[NH:26][C@H:27]1[CH2:30][C@H:29]([NH:31][C:4]2[C:5]3[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:6]=3[N:7]=[C:2]([Cl:1])[N:3]=2)[CH2:28]1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219764212,4-Dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 178454111HCID 178454111, compound

Product 1

HCID 178454119HCID 178454119, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 2,4-dichloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine (342 mg, 1.07 mmol), as prepared in Example 2, step 1, and tert-butyl((trans)-3-aminocyclobutyl)carbamate (200 mg, 1.07 mmol) in iPrOH (4 mL) was added DIPEA (0.5 mL). A stir bar was added to the reaction vessel and it was capped and heated in a reaction block at 70° C. for 2 hrs. The solvent was removed and the product was purified via flash chromatography eluting with a gradient of 12%-100% EtOAc in heptanes to afford the title compound (260 mg, 52% yield) as a pink solid.

Workup

  1. additionA stir bar was added to the reaction vessel and it
  2. customwas capped
  3. customThe solvent was removed
  4. customthe product was purified via flash chromatography
  5. washeluting with a gradient of 12%-100% EtOAc in heptanes

Sources & evidence

ORD record
ord-a9e3f8800fa3482eb1fb6524d7d583e2
Source dataset
uspto-grants-2015_05
Patent number
US09040547B2

Reaction notes

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