Water → 5-bromo-2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2281423Notes

Reaction equation

HRID 2281423 reaction equation
[Br:1][C:2]1[C:10]2[C:9](Cl)=[N:8][C:7]([Cl:12])=[N:6][C:5]=2[NH:4][CH:3]=1.[CH:13]1([NH2:17])[CH2:16][CH2:15][CH2:14]1.C(Cl)Cl.O>C(O)CCC>[Br:1][C:2]1[C:10]2[C:9]([NH:17][CH:13]3[CH2:16][CH2:15][CH2:14]3)=[N:8][C:7]([Cl:12])=[N:6][C:5]=2[NH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 75645CyclobutylamineHCID 579904405-Bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 579903055-bromo-2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 96.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-bromo-2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (142 mg, 0.530 mmol), cyclobutylamine (0.090 mL, 1.06 mmol) and TEA (0.150 mL, 1.08 mmol) in nBuOH (6 mL) was stirred at 70° C. for 18 h. CH2Cl2 and H2O were added. The organic phase was separated, washed with 5% NaHCO3, then with 1N HCl, dried over Na2SO4, concentrated in vacuo to give 5-bromo-2-chloro-N-cyclobutyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (154 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialwith 1N HCl, dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4267d5441c1c4ed8b15e3031750e6b43
Source dataset
uspto-grants-2015_09
Patent number
US09139581B2

Reaction notes

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