tert-Butanol → [4-(1-phenyl-1H-pyrazol-5-yl]pyrimidin-2-yl}amino benzoic acid

HRID 2214780Notes

Reaction equation

COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[N:16]=[C:15]([C:17]3[N:21]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:20]=[CH:19][CH:18]=3)[CH:14]=[CH:13][N:12]=2)=[CH:6][CH:5]=1.[OH-:29].[Na+].[C:31]([OH:35])(C)(C)C>O1CCOCC1>[C:22]1([N:21]2[C:17]([C:15]3[CH:14]=[CH:13][N:12]=[C:11]([NH:10][C:7]4[CH:8]=[CH:9][CH:4]=[CH:5][C:6]=4[C:31]([OH:35])=[O:29])[N:16]=3)=[CH:18][CH:19]=[N:20]2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of methyl 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoate (2-1, 60 mg, 0.16 mmol, 1 equiv) and aqueous 1N sodium hydroxide solution (0.81 mL, 0.81 mmol, 5.0 equiv) in a 1:1 mixture of t-butanol and dioxane (5 mL) was heated at 80° C. for 16 hours. The reaction mixture was partitioned between aqueous half-saturated ammonium chloride solution and ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulfate and concentrated to give 4-{[4-(1-phenyl-1H-pyrazol-5-yl)pyrimidin-2-yl]amino}benzoic acid (2-2) as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 12.50 (br s, 1H), 10.04 (s, 1H), 8.60 (d, 1H, J=4.9 Hz), 7.86 (s, 1H), 7.63 (d, 2H, J=8.2 Hz), 7.51–7.33 (m, 5H), 7.25 (d, 2H, J=8.6 Hz), 7.06 (m, 2H).

Workup

customThe reaction mixture was partitioned between aqueous half-saturated ammonium chloride solution and ethyl acetate (2×50 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-ff4b2bf1b2e54ce0a0818cac1a87d570
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109204B2

Reaction notes

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