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

HRID 1052419Notes

Reaction equation

HRID 1052419 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]=1Br.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:44]=[CH:45][CH:46]=1)[CH2:34]B1OC(C)(C)C(C)(C)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[CH2:34][C:33]1[CH:44]=[CH:45][CH:46]=[C:31]([O:30][CH3:29])[CH:32]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 114139602-[(3-Methoxyphenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 118433733HCID 118433733, compound

Product 1

HCID 118433958(S)-2-(1-((6-Amino-5-(3-methoxybenzyl)pyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-oneYield 26%

Procedure

(S)-2-(1-((6-Amino-5-bromopyrimidin-4-yl)amino)ethyl)-5-methyl-3-phenylpyrrolo[2,1-f][1,2,4]triazin-4(3H)-one (250 mg, 0.57 mmol) was treated with 2-(3-methoxybenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (211 mg, 0.85 mmol), sodium carbonate (2M, 1.28 mL, 2.56 mmol) and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (70 mg, 0.09 mmol) according to the method described in Example 3 to give 70 mg (26% yield) of the title compound as a solid. Purity 100%.

Sources & evidence

ORD record
ord-1592c66a885a47d2a4d4c6b269abf777
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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