5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90314378, compound

HRID 1524079Notes

Reaction equation

HRID 1524079 reaction equation
Br[C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([CH:11]2[CH2:13][CH2:12]2)[N:8]=[CH:7][N:6]=1.[F:18][C:19]1[CH:24]=[C:23](B2OC(C)(C)C(C)(C)O2)[CH:22]=[CH:21][C:20]=1[C:34]1[CH:35]=[N:36][C:37]([NH2:40])=[N:38][CH:39]=1>>[CH:11]1([C:9]2[N:8]=[CH:7][N:6]=[C:5]([O:4][C:3]3[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=3[C:23]3[CH:22]=[CH:21][C:20]([C:34]4[CH:39]=[N:38][C:37]([NH2:40])=[N:36][CH:35]=4)=[C:19]([F:18])[CH:24]=3)[CH:10]=2)[CH2:13][CH2:12]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 90314118HCID 90314118, compound

Product 1

HCID 90314378HCID 90314378, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 4-(2-bromophenoxy)-6-cyclopropylpyrimidine 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 C23H18FN5O, 399.15; m/z found, 399.9 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.45 (s, 1H), 8.42 (s, 2H), 7.56-7.50 (m, 2H), 7.48-7.43 (m, 1H), 7.41-7.36 (m, 1H), 7.33-7.23 (m, 3H), 6.99 (s, 1H), 6.86 (s, 2H), 2.09-2.01 (m, 1H), 1.02-0.92 (m, 4H).

Sources & evidence

ORD record
ord-6b08cc459822452bbcd0dd562e023577
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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