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Sustainable Chemical Processes

Table 3 Synthesis of butyl acrylate 7-deaza purine analogues 26-31

From: Heck and Sonogashira couplings in aqueous media – application to unprotected nucleosides and nucleotides

Entry

R 1

R 2

R 3

Starting Material

Product

Yield (%)

1

NH2

H

H

20

26

81a

2

NH2

H

PO3H2

21

27

55b

3

NH2

H

P3O9H4

22

28

43b

4

OH

NH2

H

23

29

84a

5

OH

NH2

PO3H2

24

30

38b

6

OH

NH2

P3O9H4

25

31

44b

  1. aBuCO2CHCH2 (6 eq), Pd(OAc)2 (5 mol%), TPPTS (10 mol%), NEt3 (2 eq), 1,5 h. bBuCO2CHCH2 (10 eq), Pd(OAc)2 (10 mol%), TPPTS (25 mol%), NEt3 (3 eq), 1 h.
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