(S)-4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yloxy)phenyl)-1,3,2-dioxaborolane → HCID 178504967, compound

HRID 2194596Notes

Reaction equation

HRID 2194596 reaction equation
Br[C:2]1[C:3]([O:16][CH:17]2[CH2:20][N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:18]2)=[N:4][C:5]([NH:8][C@H:9]2[CH2:14][CH2:13][C@@H:12]([CH3:15])[CH2:11][CH2:10]2)=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:33]2[CH:38]=[CH:37][C:36]([O:39][C@H:40]3[CH2:44][CH2:43][O:42][CH2:41]3)=[CH:35][CH:34]=2)O1>>[CH3:15][C@@H:12]1[CH2:13][CH2:14][C@H:9]([NH:8][C:5]2[N:4]=[C:3]([O:16][CH:17]3[CH2:20][N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:18]3)[C:2]([C:33]3[CH:38]=[CH:37][C:36]([O:39][C@H:40]4[CH2:44][CH2:43][O:42][CH2:41]4)=[CH:35][CH:34]=3)=[CH:7][N:6]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 2

HCID 71108019(S)-4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yloxy)phenyl)-1,3,2-dioxaborolaneHCID 178504965HCID 178504965, compound

Product 1

HCID 178504967HCID 178504967, compoundYield 46%

Procedure

Using the procedure of Example 1 Step 3, 5-bromo-N-(cis-4-methylcyclohexyl)-4-(1-(methylsulfonyl)azetidin-3-yloxy)pyrimidin-2-amine was reacted with (S)-4,4,5,5-tetramethyl-2-(4-(tetrahydrofuran-3-yloxy)phenyl)-1,3,2-dioxaborolane to provide the title compound (105 mg, 46% yield). 1H NMR (CDCl3, 400 MHz) 8.12 (s, 1H), 7.38 (m, 2H), 6.91 (m, 2H), 5.34 (m, 1H), 5.20 (sb, 1H), 4.95 (m, 1H), 4.31 (m, 2H), 4.09-3.92 (m, 6H), 2.90 (s, 3H), 2.22 (m, 2H), 1.80-1.57 (m, 6H), 1.23 (m, 2H), 0.94 (d, 3H). MS (ESI) m/z: Calc. 502.2 (M+). Found: 503.1 (M++1).

Sources & evidence

ORD record
ord-1f2fd54f688b4f66a0f487e025699d7f
Source dataset
uspto-grants-2012_12
Patent number
US08334292B1

Reaction notes

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