Hydrochloric Acid → HCID 178492160, compound

HRID 1621539Notes

Reaction equation

N1C=C2C(N=CN2)=NC=1.[Cl:10][C:11]1[CH:12]=[C:13]([C:26]2[N:34]=[C:33]([CH3:35])[N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][N:30]3C2CCCCO2)[C:14]([NH:17][C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[N:15][CH:16]=1.Cl.[OH-].[Na+]>C1COCC1.C(Cl)Cl>[Cl:10][C:11]1[CH:12]=[C:13]([C:26]2[N:34]=[C:33]([CH3:35])[N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][NH:30]3)[C:14]([NH:17][C:18]2[CH:19]=[N:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)=[N:15][CH:16]=1

Participants

Conditions

Temperature: 100 °C

Procedure

The title compound was prepared following the procedure described in Example 62, with the deprotection of the purine performed as follows. A glass microwave reaction vessel was charged with 5-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-amine (0.100 g, 0.221 mmol) and 1.0 M hydrochloric acid (1.106 mL, 1.106 mmol) in THF (2 ml). The reaction mixture was stirred and heated in a Discover model microwave reactor (CEM, Matthews, N.C.) at 100° C. for 10 minutes (100 watts, Powermax feature on). The mixture was diluted with DCM, made basic (pH about 12) with 1 N NaOH and allowed mixture to stir for 10 min. The precipitate was collected by filtration and washed with diethyl ether to give 5-chloro-N-(6-methoxypyridin-3-yl)-3-(2-methyl-9H-purin-6-yl)pyridin-2-amine (0.060 g, 0.163 mmol, 73.7% yield) as a yellow solid. 1H NMR (400 MHz, d6-DMSO) δ 13.83 (s, 1H); 10.24 (s, 1H); 8.54 (s, 1H); 8.18 (s, 2H); 8.06 (s, 1H); 3.85 (s, 3H); 2.73 (s, 3H); 1.62 (s, 2H). m/z (ESI, +ve ion) 367.9 (M+H)+.

Workup

customThe title compound was prepared
customA glass microwave reaction vessel
stirringto stir for 10 min
filtrationThe precipitate was collected by filtration
washwashed with diethyl ether

Sources & evidence

ORD record: ord-98328540a5dc4a81871b1da5ca1a06d5
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772480B2

Reaction notes

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