HCID 66599980, compound → HCID 178507723, compound

HRID 1811782Notes

Reaction equation

HRID 1811782 reaction equation
O1CCCCC1[N:7]1[CH:15]=[N:14][C:13]2[C:8]1=[N:9][CH:10]=[N:11][C:12]=2[C:16]1[C:17]([NH:22][C:23]2[CH:24]=[CH:25][C:26]([NH:29]C(=O)C)=[N:27][CH:28]=2)=[N:18][CH:19]=[CH:20][CH:21]=1>Cl>[N:11]1[C:12]([C:16]2[C:17]([NH:22][C:23]3[CH:28]=[N:27][C:26]([NH2:29])=[CH:25][CH:24]=3)=[N:18][CH:19]=[CH:20][CH:21]=2)=[C:13]2[C:8]([NH:7][CH:15]=[N:14]2)=[N:9][CH:10]=1

Participants

3

Reactant 1

HCID 66599980HCID 66599980, compound

Product 1

HCID 178507723HCID 178507723, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of N-(5-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-ylamino)pyridin-2-yl)acetamide (18.8 mg, 44 μmol) in 5 N aqueous HCl (1 mL) was heated at 95° C. for 1 h, after which time LCMS indicated conversion to desired product. The solution was made slightly alkaline with 5 N aqueous NaOH (about pH 8) and the resulting precipitate was collected by filtration, washing with water, and dried to give N3-(3-(9H-purin-6-yl)pyridin-2-yl)pyridine-3,6-diamine (6.0 mg, 45% yield) as a dark solid. 1H NMR (d6-DMSO, 400 MHz) δ 12.17 (bs, 1H), 9.74 (d, 1H), 8.98 (s, 1H), 8.55 (s, 1H), 8.21 (m, 2H), 7.77 (dd, 1H), 6.89 (dd, 1H), 6.49 (d, 1H), 5.65 (bs, 3H); m/z (API-ES) 305, (M+H)+.

Sources & evidence

ORD record
ord-989d60f2318d407c9a79cda1cacd5905
Source dataset
uspto-grants-2013_01
Patent number
US08362241B2

Reaction notes

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