Sodium Carbonate → (3R,4S)-1-Pyridin-3-yl-4-(4-pyrimidin-5-yl-phenoxy)pentan-3-ol

HRID 1856706Notes

Reaction equation

[OH:1][C@H:2]([CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C@H:3]([CH3:14])[O:4][C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1.Br[C:24]1[CH:25]=[N:26][CH:27]=[N:28][CH:29]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[N:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH2:16][CH2:15][C@@H:2]([OH:1])[C@@H:3]([O:4][C:5]2[CH:10]=[CH:9][C:8]([C:24]3[CH:25]=[N:26][CH:27]=[N:28][CH:29]=3)=[CH:7][CH:6]=2)[CH3:14])[CH:18]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Prepared according to the method described in Example 21b) from (1S,2R)-4-(2-hydroxy-1-methyl-4-pyridin-3-ylbutoxy)benzeneboronic acid (0.200 g, Example 21a)), 5-bromopyrimidine (0.159 g), ethanol (3 ml), 2M aqueous sodium carbonate (0.67 ml) and tetrakistriphenylphosphine palladium(0) (0.030 g) with heating at 90° C. for 4 hours. After work up, the residue was purified by reverse phase HPLC, eluting with a gradient of 15:85 to 95:5 acetonitrile in 0.1M ammonium acetate. The compound was subsequently purified by flash chromatography on silica gel, eluting with 1:1 isohexane/acetone to give the title compound as an oil (0.070 g).

Workup

customPrepared
customAfter work up, the residue was purified by reverse phase HPLC
washeluting with a gradient of 15:85 to 95:5 acetonitrile in 0.1M ammonium acetate
customThe compound was subsequently purified by flash chromatography on silica gel
washeluting with 1:1 isohexane/acetone

Sources & evidence

ORD record: ord-6fbb52769fbb4deaa6c5198bf9ee7b42
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143751

Reaction notes

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