Morpholine → HCID 25221828, compound

HRID 886817Notes

Reaction equation

[CH:1]([N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8](Cl)=[N:9][C:10]=2[C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=1)([CH2:3][CH3:4])[CH3:2].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CC(N(C)C)=O>[CH:1]([N:5]1[CH:13]=[N:12][C:11]2[C:6]1=[N:7][C:8]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[N:9][C:10]=2[C:14]1[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=1)([CH2:3][CH3:4])[CH3:2]

Participants

Conditions

Temperature: 94 °C

Procedure

To a solution of 5-(9-sec-butyl-2-chloro-9H-purin-6-yl)-pyrimidin-2-ylamine (1.12 mmol) in dimethyl acetamide (18 ml) was added morpholine (3.5 mmol). The reaction mix was heated on an oil bath maintained at 94° C. for 12 h. The reaction was monitored for the absence of the give 5-(9-sec-butyl-2-chloro-9H-purin-6-yl)-pyrimidin-2-ylamine, by LC-MS. The crude material was directly loaded onto a preparative HPLC column and purified by chromatography to get the title compound in a yield of 70%. 1H NMR, DMSO-d6: 9.52 (s, 2H); 8.27 (s, 1H); 7.28 (s, 2H); 4.5 (m, 2H); 3.8 (m, 4H); 3.70 (m, 4H); 2.0 (m, 1H); 1.9 (m, 1H); 1.6 (d, 3H); 0.79 (t, 3H). m/z: 355.45 [MH]+.

Workup

additionThe reaction mix
temperaturewas heated on an oil bath
custompurified by chromatography

Sources & evidence

ORD record: ord-2855bbf218b449fe9d4fcea986bfb464
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247410B2

Reaction notes

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