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Sustainable Chemical Processes

Table 2 Synthesis of butyl acrylate uridine and cytosine analogues 7, 15-19

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

Entry

R 1

R 2

Starting material

Product

Yield (%)

1

OH

H

1

7

98a

2

OH

PO3H2

10

15

35b

3

OH

P3O9H4

11

16

4b

4

NH2

H

12

17

16a

5

NH2

PO3H2

13

18

-b

6

NH2

P3O9H4

14

19

-b

  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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