2,6-Dimorpholin-4-ylpyridin-4-amine → N4-(5-chlorobenzo[d][1,3]dioxol-4-yl)-N2-(2,6-dimorpholinopyridin-4-yl)-N4-methylpyrimidine-2,4-diamine

HRID 2237407Notes

Reaction equation

HRID 2237407 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[C:11]([NH2:13])[CH:10]=[C:9]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:8]=2)[CH2:3][CH2:2]1.Cl[C:21]1[N:26]=[C:25]([N:27]([C:29]2[C:37]3[O:36][CH2:35][O:34][C:33]=3[CH:32]=[CH:31][C:30]=2[Cl:38])[CH3:28])[CH:24]=[CH:23][N:22]=1>>[Cl:38][C:30]1[CH:31]=[CH:32][C:33]2[O:34][CH2:35][O:36][C:37]=2[C:29]=1[N:27]([CH3:28])[C:25]1[CH:24]=[CH:23][N:22]=[C:21]([NH:13][C:11]2[CH:10]=[C:9]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:8]=[C:7]([N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)[CH:12]=2)[N:26]=1

Participants

3

Reactant 2

HCID 575713742,6-Dimorpholin-4-ylpyridin-4-amineHCID 581544482-chloro-N-(5-chlorobenzo[d][1,3]dioxol-4-yl)-N-methylpyrimidin-4-amine

Product 1

HCID 42645044N4-(5-chlorobenzo[d][1,3]dioxol-4-yl)-N2-(2,6-dimorpholinopyridin-4-yl)-N4-methylpyrimidine-2,4-diamineYield 25.3%

Procedure

2,6-Dimorpholinopyridin-4-amine (160 mg, 0.60 mmol) and 2-chloro-N-(5-chlorobenzo[d][1,3]dioxol-4-yl)-N-methylpyrimidin-4-amine (180 mg, 0.60 mmol) were reacted according to the procedure in Example 1 to give N4-(5-chlorobenzo[d][1,3]dioxol-4-yl)-N2-(2,6-dimorpholinopyridin-4-yl)-N4-methylpyrimidine-2,4-diamine (80 mg, 25.2%) as a pale yellow foam. NMR Spectrum (CDCl3) 3.23-3.58 (m, 11H), 3.72-3.90 (m, 8H), 5.65 (s, 1H), 6.03 (s, 2H), 6.50 (s, 2H), 6.79 (d, 1H), 6.99 (d, 1H), 7.17 (s, 1H), 7.90 (s, 1H); Mass spectrum: MH+ 526.

Sources & evidence

ORD record
ord-b6b513982fed4045b863ef632249e8fa
Source dataset
uspto-grants-2010_05
Patent number
US07718653B2

Reaction notes

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