Benzyl Chloride → Ethyl 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate

HRID 1525235Notes

Reaction equation

[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)[N:3]=1.[Na].OC1C(C(OCC)=O)=CN=C(N2C=CC=N2)N=1.[CH2:36](Cl)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.CCN(CC)CC>CN(C=O)C.O>[CH2:36]([O:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)[N:3]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-hydroxy-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylate, 11-a, (0.62 g, 2.7 mmol) in DMF (7 ml) were added benzyl chloride (0.5 g, 3.99 mmol) and Et3N (0.8 g, 7.97 mmol). The resulting mixture was then heated at 60° C. for 12 hours. Then it was cooled to room temperature and diluted with water followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was purified on silica gel column with the eluent of ethyl acetate/petroleum ether=1/1 (Rf=0.7) to afford the product, 11-b, (0.36 g, 42%).

Workup

temperatureThen it was cooled to room temperature
extractionfollowed by extraction with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customThe residue was purified on silica gel column with the eluent of ethyl acetate/petroleum ether=1/1 (Rf=0.7)

Sources & evidence

ORD record: ord-d55c05b77a7e4a028fd77c5ec6445ef4
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079930B2

Reaction notes

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