Cesium carbonate → HCID 60204516, compound

HRID 507616Notes

Reaction equation

[I:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][CH2:15][N:16]3[C:20]([CH3:22])([CH3:21])[C:19](=[O:23])[NH:18][C:17]3=[O:24])[N:8]=2)=[CH:4][CH:3]=1.C1(S([O-])=O)C=CC=CC=1.[Na+].C[C:36]1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)O[C:38]2[C:39](P(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:40][CH:41]=[CH:42][C:37]1=2.C(=O)([O-])[O-].[Cs+].[Cs+].C(O[K])(C)(C)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.CC(O)(C)C.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]>[CH2:36]([N:18]1[C:19](=[O:23])[C:20]([CH3:22])([CH3:21])[N:16]([CH2:15][CH2:14][NH:13][C:9]2[N:8]=[C:7]([C:5]3[S:6][C:2]([I:1])=[CH:3][CH:4]=3)[CH:12]=[CH:11][N:10]=2)[C:17]1=[O:24])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 50 mg (0.11 mmol) of 1-{2-[4-(5-iodothiophen-2-yl)pyrimidin-2-ylamino]ethyl}-5,5-dimethylimidazolidine-2,4-dione, 22 mg (0.13 mmol) of sodium benzenesulfinate, 3 mg (0.0027 mmol) of Pd2dba3, 3.5 mg (0.00547 mmol) of Xantphos, 71 mg (0.22 mmol) of cesium carbonate, 34 mg (0.109 mmol) of N-benzyl-tri-n-butylammonium chloride and 0.22 mL of a 1 M solution of tBuOK in tBuOH in 3 mL of toluene was heated to 110° C. in a microwave for 10 min. The toluene was removed in vacuo and the residue purified by C-8 prep HPLC to deliver the title compound. MS (M+H)+ 548.

Workup

customThe toluene was removed in vacuo
customthe residue purified by C-8 prep HPLC

Sources & evidence

ORD record: ord-7d16da5214f6484db02467903c3c1f06
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786132B2

Reaction notes

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