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Generated: December 15, 2017

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Title: Pyrrolo(2,3-d)pyrimidines
Abstract:3-Ethynylpyrrolo[2,3-d]pyrimidines are chemical intermediates for antineoplastic N-(acyl)glutamic acid derivatives. A typical embodiment is 3-ethynyl-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine.
Inventor(s): Taylor; Edward C. (Princeton, NJ), Kuhnt; Dietmar G. (Leverkusen, DE), Shih; Chuan (Carmel, IN), Grindey; Gerald B. (Indianapolis, IN)
Assignee: The Trustees of Princeton University (Princeton, NJ)
Filing Date:Jan 31, 1992
Application Number:07/830,111
Claims:1. A compound of the formula: ##STR8## in which: R.sup.3' is hydrogen, trimethylsilyl silyl group, or --R.sup.3 --R.sup.7 ;

R.sup.3 is phenylene, thienediyl, furanediyl, cyclohexanediyl, or alkanediyl of 2 to 4 carbon atoms;

R.sup.7 is --COOR.sup.2', --CONHCH(COOR.sub.2') CH.sub.2 CH.sub.2 COOR.sup.2'

R.sup.2' is hydrogen or carboxy protecting group;

R.sub.4', when taken independently of Z.sup.1, is hydrogen, methyl, hydroxymethyl, or hydroxymethyl substituted with a hydroxy protecting group;

R.sup.5' is hydrogen, methyl, amino, or amino carrying a protecting group; and

Z.sup.1 is hydrogen, or Z.sup.1 taken together with R.sup.4' is a carbon-carbon bond.

2. A compound of the formula: ##STR9## in which: R.sub.3' is hydrogen, trimethylsilyl silyl group, or --phenylene-R.sup.7 ;

R.sup.5 is amino, or protected amino;

R.sup.7 is --COOOR.sup.2', --CONHCH(COOR.sup.2') CH.sub.2 CH.sub.2 COOR.sup.2'); and

R.sup.2' is hydrogen or carboxy protecting group.

3. A compound according to claim 2 wherein R.sup.3' is hydrogen of trimethylsilyl silyl group.

4. A compound according to claim 1 which is a 6-lower alkanamide of 3-ethynyl-4-hydroxy-6-aminopyrrolo[2,3d]pyrimidine.

5. A compound according to claim 1 which is 3-ethynyl-4hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyrimidine.

6. A compound according to claim 1 which is 3-trimethylsilylethynyl-4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]pyimidine.

7. A compound according to claim 1 which is dimethyl N-(4-(4-hydroxy-6-pivaloylaminopyrrolo-[2,3-d]pyrimidin-3-ylethynyl)benzoy l]-L-glutamate.

8. A compound according to claim 1 which is dimethyl N-[4-(4-hydroxypyrrolo[2,3-d]pyrimidin-3-ylethynl)benzoyl]-L-glutamate.
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