5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90313481, compound

HRID 1524037Notes

Reaction equation

HRID 1524037 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:3]=1[O:4][CH2:5][O:6][CH2:7][CH2:8][Si:9]([CH3:12])([CH3:11])[CH3:10].[F:21][C:22]1[CH:27]=[C:26](B2OC(C)(C)C(C)(C)O2)[CH:25]=[CH:24][C:23]=1[C:37]1[CH:38]=[N:39][C:40]([NH2:43])=[N:41][CH:42]=1>>[F:21][C:22]1[CH:27]=[C:26]([C:2]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:3]=2[O:4][CH2:5][O:6][CH2:7][CH2:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH:25]=[CH:24][C:23]=1[C:37]1[CH:42]=[N:41][C:40]([NH2:43])=[N:39][CH:38]=1

Participants

3

Reactant 2

HCID 903131425-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amineHCID 90313430HCID 90313430, compound

Product 1

HCID 90313481HCID 90313481, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using (2-((2-bromo-5-(trifluoromethyl)phenoxy)methoxy)ethyl)trimethylsilane and 5-(2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-pyrimidin-2-amine. MS (ESI): mass calcd. for C23H25F4N3O2Si, 479.17; m/z found, 480.0 [M+H]+. 1H NMR (500 MHz, CD3OD) δ 8.55-8.48 (m, 2H), 7.60-7.51 (m, 3H), 7.48-7.36 (m, 3H), 5.33-5.29 (d, J=1.0, 2H), 3.73-3.66 (m, 2H), 0.93-0.84 (t, J=8.0, 2H), −0.03-−0.07 (m, 9H).

Sources & evidence

ORD record
ord-81c56259db7745d98ce866fb1971e799
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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