1,4-Bis(dihydroquinidine)phthalazine → (R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol

Participants

Role	Name	HCID	Charge
Reactant	1,4-Bis(dihydroquinidine)phthalazine	HCID 11217202	—
Reactant	4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine	HCID 57713816	—
Reactant	2-Methylpropan-2-ol--water (1/1)	HCID 71401949	—
Product	(R)-4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbut-3-yne-1,2-diol	HCID 57713869	—

Reaction Steps

Treatment of 4-cloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-5-(3-methylbut-3-en-1-ynyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine (see example 51) (357 mg) with AD-mix-β (Aldrich, 1.57 g) in t-BuOH:water 1:1: (10 mL) at rt for 18 h, followed by quench (NaHSO3, 1.2 g), work-up, and silica gel flash chromatography (1→10% MeOH in DCM) gave the title compound (61 mg) and recovered starting material (263 mg). Solid. HPLC Rt=4.36 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093229B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-fa81cf2c45ee49198b822c572b928636
Source note	uspto-grants-2012_01