Methanol → 4-(4-Tert-butoxycarbonylamino-naphthalen-1-yloxy)-pyrimidine-2-carboxylic acid methyl ester

HRID 23535Notes

Reaction equation

[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21](I)[N:20]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:27][OH:28].CCN(CC)CC.CN([CH:39]=[O:40])C>CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[CH3:27][O:28][C:39]([C:21]1[N:20]=[C:19]([O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:26])=[CH:9][CH:10]=2)[CH:24]=[CH:23][N:22]=1)=[O:40]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of [4-(2-iodo-pyrimidin-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester (100 mg, 0.44 mmol) in 2 mL of DMF, was added, 0.5 mL MeOH, 0.12 mL of Et3N (0.9 mmol), Pd(OAc)2 (10 mg, 0.04 mmol), and DPPF (44 mg, 0.4 mmol). The reaction was heated under a CO balloon at 60° C. for 5 h. The reaction was then diluted with EtOAc, concentrated in vacuo on silica gel and chromatographed directly with 10-80% EtOAc-hexanes to provide 26 mg (14%) of 4-(4-tert-butoxycarbonylamino-naphthalen-1-yloxy)-pyrimidine-2-carboxylic acid methyl ester as a brown solid.

Workup

concentrationconcentrated in vacuo on silica gel
customchromatographed directly with 10-80% EtOAc-hexanes

Sources & evidence

ORD record: ord-c3449052d0384447ac601160bd40f9ae
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852717B2

Reaction notes

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