Cesium carbonate → HCID 123832164, compound

HRID 1497355Notes

Reaction equation

Br[C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][N:3]=1.[CH3:16][O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:25]2[CH2:26][CH2:27][CH2:28][CH:24]2[NH:23][C:22]1=[O:29].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[CH3:16][O:17][CH2:18][CH2:19][CH2:20][N:21]1[CH:25]2[CH2:26][CH2:27][CH2:28][CH:24]2[N:23]([C:2]2[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][N:3]=2)[C:22]1=[O:29]

Participants

Conditions

Temperature: 90 °C

Procedure

In a 10 mL pyrex tube, 2-bromo-5-(phenylethynyl)pyrimidine (CAS: 1338493-52-9)(80 mg, 309 μmol, Eq: 1.00) and (rac)-(3aRS,6aSR)-1-(3-Methoxy-propyl)-hexahydro-cyclopentaimidazol-2-one (68.0 mg, 309 μmol, 1.0 equiv.) were dissolved in 2 ml of Toluene. Cesium carbonate (201 mg, 618 μmol, 2.0 equiv.), Xanthphos (7.15 mg, 12.4 μmol, 0.04 equiv.) and Pd2(dba)3 (5.65 mg, 6.18 μmol, 0.02 equiv.) were added and the red-brown reaction mixture was stirred at 90° C. for 3 hr. The reaction mixture was filtered, adsorbed on silica, and purified by flash chromatography (silica gel, 20 g with 1 g Silica-NH2, 30% to 100% EtOAc in heptane gradient at 301 nm). One obtained 65.6 mg of the title compound as a yellow oil; MS: m/e=377.6 (M+H+).

Workup

filtrationThe reaction mixture was filtered
custompurified by flash chromatography (silica gel, 20 g with 1 g Silica-NH2, 30% to 100% EtOAc in heptane gradient at 301 nm)

Sources & evidence

ORD record: ord-6f32f9b859864822b6b07a6be8c26860
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199971B2

Reaction notes

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