Diisopropylethylamine → N-(6-(Trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydro-6-(3-(methylsulfonyl)pyridin-2-yl)pyrido[4,3-d]pyrimidin-4-amine

HRID 535354Notes

Reaction equation

HRID 535354 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:19][NH:18][CH2:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C>>[F:21][C:2]([F:20])([F:1])[C:3]1[N:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:19][N:18]([C:23]4[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=4)[CH2:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 125137462-Chloro-3-(methanesulfonyl)pyridineHCID 59346451N-(6-(Trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Product 1

HCID 59346520N-(6-(Trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydro-6-(3-(methylsulfonyl)pyridin-2-yl)pyrido[4,3-d]pyrimidin-4-amine

Procedure

The title compound was prepared according to the procedure described for Compound 4 and reacting N-(6-(trifluoromethyl)pyridin-3-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (140 mg, 0.47 mmol) with 2-chloro-3-(methylsulfonyl)pyridine (Ponticello, JOC, 44(17), 1979) (0.115 g, 0.06 mmol) in the presence of N,N-diisopropylethylamine (0.17 mL, 0.98 mmol) to give the desired Compound 5 as an off-white powder (55 mg, 26%).

Sources & evidence

ORD record
ord-28456416eb8f473a8c90809e4e3d9ec4
Source dataset
uspto-grants-2014_10
Patent number
US08859545B2

Reaction notes

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