Pyrazole → HCID 59729280, compound

HRID 600468Notes

Reaction equation

HRID 600468 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14](Cl)[C:9]=2[NH:8][CH:7]=1)=[O:5])[CH3:2].[NH:16]1[CH:20]=[CH:19][CH:18]=[N:17]1>O1CCOCC1>[N:16]1([C:14]2[C:9]3[NH:8][CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:10]=3[N:11]=[CH:12][N:13]=2)[CH:20]=[CH:19][CH:18]=[N:17]1

Participants

4

Reactant 2

HCID 1048PyrazoleHCID 52987614Ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Product 1

HCID 59729280HCID 59729280, compoundYield 14.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a sealed tube 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carbonyl chloride 5 (2.0 g, 8.9 mmol), pyrazole (1.8 g, 26.5 mmol) and 1,4 dioxane (10 mL) were heated at 138° C. for 2 h. Upon cooling to ambient temperature a precipitate formed which was collected and washed with saturated aqueous NaHCO3 and diethyl ether to yield 49 (340 mg, 1,3 mmol) as a white solid. The filtrate was treated with saturated aqueous NaHCO3 (20 ml) and the resulting precipitate was washed with saturated aqueous NaHCO3 and diethyl ether to yield additional 49 (2.0 g, 7.8 mmol, 99% total yield). 1H NMR: (500 MHz, CD3OD) δ 8.99 (br s, 1H), 8.78 (br s, 1H), 8.29 (s, 1H), 8.06 (br s, 1H), 6.72 (br s, 1H), 4.30 (q, J=7.0 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H); LC/MS: (ES+) m/z (M+H)+=258; HPLC Rt=1.20 min., column L.

Workup

  1. customformed which
  2. customwas collected
  3. washwashed with saturated aqueous NaHCO3 and diethyl ether

Sources & evidence

ORD record
ord-8611c591e28a40fcabe34ef4e797ce62
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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