ChemicalBook CAS DataBase List 5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-propyl-

5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-propyl- synthesis

2synthesis methods

Product Name:5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-propyl-
CAS Number:1415346-17-6
Molecular formula:C9H10ClN3
Molecular Weight:195.65

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106-94-5 Synthesis

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5H-Pyrrolo[3,2-d]pyrimidine, 2-chloro-5-propyl-

1415346-17-6
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Yield:1415346-17-6 74.6%

Reaction Conditions:

with caesium carbonate in N,N-dimethyl-formamide at 25; for 4 h;

Steps:

100

1-Bromopropane (132 mg, 1.074 mmol) was added to a solution of product of Example 1001 (150 mg, 0.977 mmol) in DMF (10 mL) followed by cesium carbonate (0.477 g, 1.074 mmol), and the mixture was stirred at 25 °C for 4 h. Insoluble solids were filtered off, and filtrate was concentrated. Residue was partitioned between ethyl acetate and water. Organic layer was separated, washed with brine, dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography using 5% ethyl acetate in hexane to afford title compound (0.15 g, 74.6%) as a brown color syrup. 1H NMR (300MHz, CDC1₃): δ 8.68 (s, 1H), 7.51 (d, J = 3.0 Hz, 1H), 6.62 (d, J = 2.7 Hz, 1H), 4.16 (t, J = 6.9 Hz, 2H), 1.91 (m, 2H), 0.94 (t, J = 7.5 Hz, 3H).

References:

WO2012/162129,2012,A1 Location in patent:Page/Page column 103

5-Pyrimidinamine, 2-chloro-4-[(1E)-2-ethoxyethenyl]-

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References