5-(2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrimidin-2-amine → HCID 90314297, compound

HRID 1524029Notes

Reaction equation

HRID 1524029 reaction equation
[N:1]1([C:5]2[CH:10]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3Br)[N:8]=[CH:7][N:6]=2)[CH2:4][CH2:3][CH2:2]1.[F:19][C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[CH:22][C:21]=1[C:35]1[CH:36]=[N:37][C:38]([NH2:41])=[N:39][CH:40]=1>>[N:1]1([C:5]2[N:6]=[CH:7][N:8]=[C:9]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:24]3[CH:23]=[CH:22][C:21]([C:35]4[CH:40]=[N:39][C:38]([NH2:41])=[N:37][CH:36]=4)=[C:20]([F:19])[CH:25]=3)[CH:10]=2)[CH2:4][CH2:3][CH2:2]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 90313689HCID 90313689, compound

Product 1

HCID 90314297HCID 90314297, compound

Procedure

The title compound was prepared in a manner similar to that described in Example 88 using 4-(azetidin-1-yl)-6-(2-bromophenoxy)pyrimidine 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 C23H19FN6O, 414.16; m/z found, 415.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 8.46 (d, J=1.5, 2H), 8.11 (d, J=0.9, 1H), 7.60-7.52 (m, 2H), 7.50-7.41 (m, 1H), 7.41-7.31 (m, 3H), 7.17 (dd, J=8.1, 1.2, 1H), 6.89 (s, 2H), 5.73 (d, J=0.9, 1H), 3.98 (t, J=7.5, 4H), 2.41-2.27 (m, 2H).

Sources & evidence

ORD record
ord-874df951a2044f40b151b6ff558e5c80
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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