3-(Tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propan-1-amine → N-(3-(tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	3-(Tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propan-1-amine	HCID 68294312	—
Reactant	(3,4-Dichlorophenyl)(oxazol-5-yl)methanamine hydrochloride	HCID 68294638	—
Reactant	N-(tetrahydro-2H-pyran-4-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-amine	HCID 71743546	—
Product	N-(3-(tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide	HCID 131733487	31.9%

Reaction Steps

Condensation of 306 and 72 was carried out in accord with the procedure described in step 6 of example 1 except 72 was used in place of 28 and 306 was used in place of 22. The crude product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:5 to 500:8) to afford 0.11 g (31.9%) of N-(3-(tert-butyldimethylsilyloxy)-1-(3,4-difluorophenyl)propyl)-2-(isopropylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxamide (308). The silyl group was removed with TBAF in accord with the procedure described in step 5 of example 42. The product was purified by SiO2 chromatography eluting with a DCM/MeOH gradient (500:15-500:25) to afford 0.010 g (12.8%) of I-77: MS m/z (APCI-pos) M+1=406.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133187B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-e6a9ab69a7e44f2a823188db43ebadb6
Source note	uspto-grants-2015_09