Methanol → 4-Chloro-5-(cyclopropylmethoxy)-2-(methylsulfonylmethyl)pyrimidine

HRID 575623Notes

Reaction equation

[CH:1]1([CH2:4][O:5][C:6]2[C:7](O)=[N:8][C:9]([CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.O=P(Cl)(Cl)[Cl:20].CO>CC#N.[N+](C)(C)(C)C.[Cl-]>[Cl:20][C:7]1[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:11][N:10]=[C:9]([CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To the title compound of step 1 (1.9 g, 7.36 mmol) in MeCN (30 mL) was added Me4NCl (1.6 g, 14.72 mmol) and POCl3 (6.8 g, 44.16 mmol). The mixture was heated at 80° C. for 6 h. After concentration under vacuum, the residue was subjected to EA extractive work up. Trituration with methanol (20 mL) gave the title compound (1 g, yield: 49.3%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 7.60 (s, 1H), 5.50 (s, 2H), 3.85 (d, J=6.8 Hz, 2H), 3.09 (s, 3H), 1.31-1.28 (m, 1H), 0.70-0.65 (m, 2H), 0.39-0.36 (m, 2H). LCMS: 277.1 (M+H)+

Workup

concentrationAfter concentration under vacuum

Sources & evidence

ORD record: ord-15bb48ee64264de891d459eec8cc7284
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034900B2

Reaction notes

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