4-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amine → 9-(2-Amino-4-methyl-pyrimidin-5-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide

HRID 708023Notes

Reaction equation

HRID 708023 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH:22]([CH3:24])[CH3:23])[C:5]([C:7]1[S:8][C:9]2[CH2:10][CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:14]=3[C:15]=2[N:16]=1)=[O:6].[CH3:25][C:26]1[C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=[C:28]([NH2:41])[N:27]=1>>[OH:1][CH2:2][CH2:3][N:4]([CH:22]([CH3:24])[CH3:23])[C:5]([C:7]1[S:8][C:9]2[CH2:10][CH2:11][O:12][C:13]3[CH:20]=[CH:19][C:18]([C:31]4[C:26]([CH3:25])=[N:27][C:28]([NH2:41])=[N:29][CH:30]=4)=[CH:17][C:14]=3[C:15]=2[N:16]=1)=[O:6]

Participants

3

Reactant 2

HCID 529879064-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyrimidin-2-amineHCID 582040029-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide

Product 1

HCID 582040659-(2-Amino-4-methyl-pyrimidin-5-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amideYield 1.1%

Procedure

Following the procedure for 277, 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid (2-hydroxy-ethyl)-isopropyl-amide (52.2 mg, 0.127 mmol) and 4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidin-2-amine (35.8 mg, 0.152 mmol) were reacted to give 278 (0.6 mg, 1% yield M+1 440.1)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-229b26c4db1749b2a94b85f340eeadee
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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