Sodium hydride → HCID 85873129, compound

HRID 748503Notes

Reaction equation

[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[C:17](Cl)[N:16]=[CH:15][N:14]=1>CN(C)C=O>[Cl:12][C:13]1[N:14]=[CH:15][N:16]=[C:17]([O:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][O:7][CH2:6][CH2:5]2)[CH:18]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of N-(2-hydroxyethyl)morpholine (1.09 g, 8.27 mmol) in N,N-dimethylformamide (5 mL) was added sodium hydride (364 mg, 9.10 mmol, 60% dispersion in oil) in portions. The mixture was stirred at room temperature for 1 h and at 45° C. for 1.5 h. The greenish solution was added dropwise over 5 min to a solution of 4,6-dichloropyrimidine (3.0 g, 20.1 mmol) in N,N-dimethylformamide (5 mL). The solvent was removed in vacuo, and the residue was partitioned between water and ethyl acetate. The organic layer was dried (Na2SO4) and the solvent was removed in vacuo. The crude product was purified on a silica gel column using ethyl acetate as the eluent affording 1.17 g (58% yield) of the title compound as a yellow oil: 1H NMR (CDCl3, 400 MHz) δ 8.57 (s, 1H), 6.80 (s, 1 H), 4.53 (t, J=6 Hz, 2 H), 3.72 (t, J=5 Hz, 4 H), 2.77 (t, J=6 Hz, 2 H), 2.55 (t, J=4 Hz, 4 H); 13C NMR (CDCl3, 100 MHz) δ 170.0, 160.7, 158.1, 108.0, 66.9, 64.6, 57.1, 53.9; MS (ESP) m/z 244 (M++1).

Workup

customThe solvent was removed in vacuo
customthe residue was partitioned between water and ethyl acetate
dry with materialThe organic layer was dried (Na2SO4)
customthe solvent was removed in vacuo
customThe crude product was purified on a silica gel column

Sources & evidence

ORD record: ord-06c63c904a0a44ac964f7ead2d663378
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07399780B2

Reaction notes

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