Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate → 5-(6-Methoxycarbonyl-2,2-dimethyl-2,3-dihydro-benzofuran-4-yloxy)-pyrimidine-2-carboxylic acid tert-butyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:18]=[N:19]C(C(=O)N(C)C)=CC=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[C:28]([O:32][C:33]([C:35]1N=CC(Br)=[CH:37][N:36]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29].COC(C1C=C(O)C2CC(C)(C)OC=2C=1)=O>>[C:28]([O:32][C:33]([C:35]1[N:19]=[CH:18][C:17]([O:16][C:14]2[C:8]3[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=3[CH:6]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:15]=2)=[CH:37][N:36]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner as described for Intermediate 161b, from 5-bromo-pyrimidine-2-carboxylic acid tert-butyl ester (171a) (497 mg, 1.92 mmol) and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e) (426 mg, 1.92 mmol) to give a yellow oil (83 mg, 11% yield). 1H NMR (400 MHz, CDCl3) δ 8.57 (s, 2 H) 7.30 (d, J=1.26 Hz, 1 H) 7.19 (d, J=1.26 Hz, 1 H) 3.88 (s, 3 H) 2.92 (s, 2 H) 1.68 (s, 9 H) 1.50 (s, 6 H); LCMS for C21H24N2O6 m/z 345.00 (M-tBu+H+).
Sources & evidence
- ORD record
- ord-3fd8093eac9b4a1c8ddb3cedc816fa8e
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08119624B2
Reaction notes
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