Sodium Carbonate → (S)-2-(1-((6-Amino-5-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one

HRID 1052754Notes

Reaction equation

HRID 1052754 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.CC1(C)C(C)(C)OB([C:37]2[CH:38]=[N:39][N:40]([CH2:42][CH2:43][OH:44])[CH:41]=2)O1.C(=O)([O-])[O-].[Na+].[Na+]>>[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]=1[C:37]1[CH:38]=[N:39][N:40]([CH2:42][CH2:43][OH:44])[CH:41]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 457888552-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-olHCID 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

Product 1

HCID 90103119(S)-2-(1-((6-Amino-5-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 8.8%

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, 0.12 mmol) was treated with 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol (66 mg, 0.28 mmol, prepared according to Perry, Benjamin Garfield; Sabin, Verity Margaret from PCT Int. Appl. (2009), WO 2009122148 A1 20091008), sodium carbonate (2M, 565 μl, 1.13 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (13 mg, 0.02 mmol) according to the method described in Example 3 to give 5 mg (8% yield) of the title compound. Purity 92%.

Sources & evidence

ORD record
ord-02ebe94efc164d33a0aed35e127dc825
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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