Diethanolamine → HCID 57877817, compound

HRID 1091401Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][C@@H:16]([C:20]4[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=4[O:28][CH3:29])[CH2:15]3)[N:11]([CH3:30])[C:10](=[O:31])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH:32](CCO)[CH2:33]CO>CNC=O>[C:26]([C:24]1[CH:23]=[CH:22][C:21]([O:28][CH3:29])=[C:20]([C@@H:16]2[O:17][CH2:18][CH2:19][N:14]([C:12]3[N:11]([CH3:30])[C:10](=[O:31])[CH:9]=[C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:32][CH3:33])[CH:7]=4)[N:13]=3)[CH2:15]2)[CH:25]=1)#[N:27]

Participants

Conditions

Temperature: 150 °C

Procedure

A suspension of 6-(2-chloropyridin-4-yl)-2-((2S)-2-(5-cyano-2-methoxyphenyl) morpholin-4-yl)-3-methyl-3H-pyrimidin-4-one obtained in Example 10-1 (0.80 g, 1.83 mmol), and diethanolamine (1.0 g, 9.51 mmol) in N-methylformamide (8 ml) was heated at 150° C. for 48 hours. The resulting suspension was partitioned between chloroform and brine and the aqueous layer was extracted with chloroform. The combined organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography eluting 5-10% methanol in chloroform to furnish 2-((2S)-2-(5-cyano-2-methoxyphenyl)-morpholin-4-yl)-3-methyl-6-(2-methylaminopyridin-4-yl)-3H-pyrimidin-4-one (0.036 g, 0.084 mmol, 5.0%) as white crystals.

Workup

customThe resulting suspension was partitioned between chloroform and brine
extractionthe aqueous layer was extracted with chloroform
washThe combined organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography
washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record: ord-91e9ff075c5e46368463f0846a1c4132
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129377B2

Reaction notes

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