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58149185909
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This compound was prepared from 2-chloro-6-iodo-9H-purine using the Mitsonobu reaction procedure described in the following reference: Toyota, N, Katagari, A, Kanebo, C Synth. Commun. 1993, 23, 1295
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This compound was prepared from 2-chloro-6-iodo-9H-purine using the Mitsonobu reaction procedure described in the following reference: Toyota, N.; Katagari, A.; Kanebo, C Synth. Commun. 1993, 23, 1295.
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40
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58149198391
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Typical Procedure. Synthesis of 4-(2,6-Dimethoxypyrimidin-4-yl) morpholine (7a, A dry and argon-flushed 50 mL flask, equipped with a magnetic stirrer and a septum, was charged with a solution of 2,4-dimethoxypyrimidine (4a; 280 mg, 2 mmol. 1 equiv) in dry THF (1 mL, After the mixture was cooled to -40°C, TMPMgCl•LiC1 (1.20 M in THF; 1.84 mL, 1.1 mmol) was added dropwise and stirred for 12 h at -40°C. The resulting Grignard reagent was then added dropwise to a solution of CuCl•2LiCl (1.0 M in THF; 2.4 mL, 2.4 mmol, 1.2 equiv) and bis[2-(N,N-dimethylamino)ethy1] ether (284 mg, 2.4 mmol, 1.2 equiv) at -50°C and was stirred for 45 min affording the corresponding copper reagent 5a. N-Lithium morpholide (6a; 4 mmol) was added dropwise and the mixture was further stirred for 1 h at -60°C. The reaction mixture was cooled to -78°C, then chloranil (590 mg, 2.4 mmol) in dry THF 14 mL, was slowly added over a period of 1 h. The r
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2, pentane/ether; 4:1) affording the aminated pyrimidine 7a (341 mg, 76%) as a gray solid (mp 93.9-95.7°C).
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