Sodium Carbonate → HCID 73776215, compound

HRID 1052758Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[C:3]=1I.[F:29][C:30]([F:51])([F:50])[S:31]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[C:37](B2OC(C)(C)C(C)(C)O2)[CH:36]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+]>>[NH2:1][C:2]1[C:3]([C:39]2[CH:40]=[C:35]([NH:34][S:31]([C:30]([F:29])([F:50])[F:51])(=[O:33])=[O:32])[CH:36]=[CH:37][CH:38]=2)=[C:4]([NH:8][C@H:9]([C:11]2[N:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:15](=[O:23])[C:14]3=[C:24]([CH3:27])[CH:25]=[CH:26][N:13]3[N:12]=2)[CH3:10])[N:5]=[CH:6][N:7]=1

Participants

Reactant 3

HCID 10340Sodium Carbonate

HCID 118433756(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HCID 131736257HCID 131736257, compound

Product 1

HCID 73776215HCID 73776215, compoundYield 42.8%

Procedure

(S)-2-(1-((6-Amino-5-iodopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (70 mg, 0.14 mmol) was treated with 1,1,1-trifluoro-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide (124 mg, 0.22 mmol, prepared according to WO 2012013727 A1 20120202), sodium carbonate (2M, 215 μl, 0.43 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (8.3 mg, 0.01 mmol) according to the method described in Example 3 to give 35 mg (42% yield) of the title compound. Purity 99%.

Sources & evidence

ORD record: ord-f6f496108edc43f2baaea1d3ccfd3fc6
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388189B2

Reaction notes

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