Paul R O'Shea

US Patent:

20200369670, Nov 26, 2020

Filed:

May 7, 2020

Appl. No.:

16/869512

Inventors:

- South San Francisco CA, US
Nicholas Andrew White - San Francisco CA, US
Haiming Zhang - San Mateo CA, US
Francis Gosselin - San Mateo CA, US
William Nack - Glenview IL, US
Paul D. O'Shea - Princeton NJ, US

Assignee:

Genentech, Inc. - South San Francisco CA

International Classification:

C07D 487/04
C07F 9/24

Abstract:

A method of regio-selectively synthesizing an imidazo-pyrimidine compound of formulae (XXa) or (XXb)comprising a step of coupling a first compound of formula XX-P1a or XX-P1b with a second compound of formula XX-P2This annulation reaction between β-ethoxy acrylamides and phosphorylated aminoimidazoles to furnish imidazo[1,2-a]pyrimidin-amines relies on steering effects from endocyclic and exocyclic phosphorylated aminoimidazoles. The reaction furnishes either 2-amino or 4-amino constitutional isomers of imidazo[1,2-a]pyrimidines with good yields and ranges of 90:10-99:1 regio-selectivity. The reaction is useful in the synthesis of various tracer molecules used in the study of neurological conditions such as where Rand Rtogether with the imidazole ring atoms to which they are bonded form a phenyl ring and the products are substituted benzimidazopyrimidines. The reaction can be generalized to form imidazo[1,2-a]pyrimidines substituted at either of their 2- and 4-positions by alkoxy or thioalkyl groups.

US Patent:

20200354369, Nov 12, 2020

Filed:

May 7, 2020

Appl. No.:

16/869475

Inventors:

- South San Francisco CA, US
Nicholas Andrew White - San Francisco CA, US
Haiming Zhang - San Mateo CA, US
Francis Gosselin - San Mateo CA, US
William Nack - Glenview IL, US
Paul D. O'Shea - Princeton NJ, US

Assignee:

Genentech, Inc. - South San Francisco CA

International Classification:

C07D 487/04

Abstract:

A method of synthesizingcomprising a step of making an imidazo-pyrimidine compound by coupling a first compound of formula (II) with a second compound of formula (III)Followed by a deprotection and tosylation step. The methods are able to produce an isotopically substituted molecule having upwards of 95% purity relative to non-isotopically substituted molecules.The invention further comprises compounds of formula: