Methanol → 5,6,7,8-Tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[4,3-d]pyrimidin-4-amine

HRID 19635Notes

Reaction equation

C(C1N[CH2:27][C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH:16][C:17]3[CH:26]=[CH:25][C:20]4[O:21][CH2:22][CH2:23][O:24][C:19]=4[CH:18]=3)[C:10]=2[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+:32].[CH3:33]O>O.[Pd]>[O:21]1[CH2:22][CH2:23][O:24][C:19]2[CH:18]=[C:17]([NH:16][C:15]3[C:10]4[CH2:9][NH:32][CH2:33][CH2:27][C:11]=4[N:12]=[CH:13][N:14]=3)[CH:26]=[CH:25][C:20]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 6-benzyl-5,6,7,8-tetrahydro-N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)pyrido[3,4-d]pyrimidin-4-amine (0.742 g, 1.98 mmol), ammonium formate (1.25 g, 19.83 mmol) and palladium, 10% wt. on activated carbon (75 mg) in methanol (10 mL) is heated to 60° C. for 2 h. The mixture is cooled to r.t. and filtered over celite. The filtrate is concentrated under reduced pressure to give a white solid which is dissolved in water. The mixture is extracted twice with a 3:1 mixture of chloroform: isoproanol. The combined organic extracts are dried over sodium sulfate and concentrated to dryness to give the title compound.

Workup

temperatureThe mixture is cooled to r.t.
filtrationfiltered over celite
concentrationThe filtrate is concentrated under reduced pressure
customto give a white solid which
extractionThe mixture is extracted twice with a 3:1 mixture of chloroform
dry with materialThe combined organic extracts are dried over sodium sulfate
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-6188faae7f2e4ca484e547d755af76d4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745451B2

Reaction notes

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