Ethyl bromoacetate → HCID 22347222, compound

HRID 432253Notes

Reaction equation

HRID 432253 reaction equation
[H-].[Na+].[I:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[N:10][C:11]=2[NH2:13])[NH:6][N:5]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O>[NH2:13][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[N:6]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:5]=[C:4]([I:3])[C:12]=12

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178508725HCID 178508725, compound

Product 1

HCID 22347222HCID 22347222, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 0.138 g, 3.45 mmol) was added to a suspension of 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.750 g, 2.87 mmol) in N,N-dimethylformamide (9 mL), and the mixture was stirred at ambient temperature for 1 hour until a homogeneous solution was obtained. Ethyl bromoacetate (0.447 mL, 4.03 mmol) was added, and the mixture was stirred at ambient temperature under an atmosphere of nitrogen for 14 hours. The solvent was removed under reduced pressure and the resulting solid was triturated sequentially with water (25 mL) and then ether/petroleum ether (4:1, 50 mL) to yield ethyl 2-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (0.791 g, 2.28 mmol) as a brown solid: 1H NMR (DMSO-d6, 400 MHz) δ 8.21 (s, 1H), 5.17 (s, 2H), 4.15 (qt, 2H), 1.20 (t, 3H); RP-HPLC (25 to 100% CH3CN in 0.1 M aqueous ammonium acetate over 10 min at 1 mL/min using a Hypersil HS C18, 250×4.6 mm column) Rt 6.87 min.

Workup

  1. customwas obtained
  2. stirringthe mixture was stirred at ambient temperature under an atmosphere of nitrogen for 14 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe resulting solid was triturated sequentially with water (25 mL)

Sources & evidence

ORD record
ord-b87939ee5bda4d0b9bb9deb7edae8d6d
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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