Morpholine → N-[4-(benzyloxy)-3-methylphenyl]-3-(2-morpholin-4-ylethoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 550519Notes

Reaction equation

HRID 550519 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:17]2[C:12](=[N:13][CH:14]=[N:15][C:16]=2[NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[C:21]([CH3:33])[CH:20]=2)[NH:11][N:10]=1)(=O)=O.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:16]2[N:15]=[CH:14][N:13]=[C:12]3[NH:11][N:10]=[C:9]([O:8][CH2:7][CH2:6][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[C:17]=23)=[CH:20][C:21]=1[CH3:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86620009HCID 86620009, compound

Product 1

HCID 67020641N-[4-(benzyloxy)-3-methylphenyl]-3-(2-morpholin-4-ylethoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 58%

Procedure

The procedure described in Example 55 was repeated using 2-[(4-{[4-(benzyloxy)-3-methylphenyl]amino}-1H-pyrazolo[3,4-d]pyrimidin-3-yl)oxy]ethyl methanesulfonate (prepared as described in Example 110) and morpholine to give the title compound in 58% yield; NMR Spectrum: 2.22 (s, 3H), 2.50-2.52 (m, 4H), 2.79 (t, 2H), 3.54-3.56 (m, 4H), 4.42 (t, 2H), 5.14 (s, 2H), 7.02 (d, 1H), 7.32-7.48 (m, 7H), 8.20 (s, 1H), 8.24 (s, 1H); Mass Spectrum: 461 (MH+).

Sources & evidence

ORD record
ord-8d7b26efe52b4eb482d04dff0e0cd14a
Source dataset
uspto-grants-2011_05
Patent number
US07947676B2

Reaction notes

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