Water → 4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidin-5-amine

HRID 1470305Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:14](C(O)=O)=[CH:13][N:12]=[C:11]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:25](CC)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.O>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([NH2:25])=[CH:13][N:12]=[C:11]([N:18]2[CH:22]=[CH:21][CH:20]=[N:19]2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 66 °C

Procedure

4-(benzyloxy)-2-(1H-pyrazol-1-yl)pyrimidine-5-carboxylic acid, 2-e, (200 mg, 0.68 mmol) was dissolved in THF (20 ml) and treated with Et3N (204 mg, 2.02 mmol) and DPPA (204 mg, 0.74 mmol). The mixture was heated at 66° C. for 12 hours. Then water was added and the resulting mixture was continued to stir at reflux for 2 h. After that the mixture was concentrated under vacuum. The residue was diluted with aq. K2CO3 followed by extraction with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The residue was purified on silica gel column with the eluent of dichloromethane/methanol=50/1 (Rf=0.7) to provide compound 2-f (72 mg, 40%).

Workup

temperatureat reflux for 2 h
concentrationAfter that the mixture was concentrated under vacuum
additionThe residue was diluted with aq. K2CO3
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under vacuum
customThe residue was purified on silica gel column with the eluent of dichloromethane/methanol=50/1 (Rf=0.7)

Sources & evidence

ORD record: ord-a836f304520b4c18867d50e2c9a318ea
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006433B2

Reaction notes

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