(2-Aminopyrimidin-5-yl)boronic acid → HCID 58234065, compound

HRID 391048Notes

Reaction equation

HRID 391048 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[S:10][C:9]([CH2:11][N:12]([CH:17]3[CH2:22][CH2:21][N:20]([CH:23]([CH3:25])[CH3:24])[CH2:19][CH2:18]3)[CH2:13][CH2:14][O:15][CH3:16])=[CH:8][C:6]=2[N:7]=1.[NH2:32][C:33]1[N:38]=[CH:37][C:36](B(O)O)=[CH:35][N:34]=1>CCOCC>[CH:23]([N:20]1[CH2:21][CH2:22][CH:17]([N:12]([CH2:11][C:9]2[S:10][C:5]3[C:4]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[N:3][C:2]([C:36]4[CH:35]=[N:34][C:33]([NH2:32])=[N:38][CH:37]=4)=[N:7][C:6]=3[CH:8]=2)[CH2:13][CH2:14][O:15][CH3:16])[CH2:18][CH2:19]1)([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 17750211(2-Aminopyrimidin-5-yl)boronic acidHCID 87209431HCID 87209431, compound

Product 1

HCID 58234065HCID 58234065, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-(1-isopropyl-piperidin-4-yl)-(2-methoxy-ethyl)-amine was reacted with 2-aminopyrimidine-5-boronic acid in General Procedure A. Acid/base work-up and trituration with ether yielded 334. 400 MHz, 1H NMR CDCl3: 9.30 (s, 2H), 7.26 (s, 1H), 5.22 (br s, 2H, NH2), 4.06 (s, 2H), 4.05 (t, 4H, J 4.4), 3.90 (t, 4H, J4.6), 3.50 (t, 2H, J6.0), 3.32 (s, 3H), 2.94 (d, 2H, J 11.2), 2.85 (t, 2H, J 6.1), 2.75-2.68 (m, 1H), 2.61-2.55 (m, 1H), 2.10 (t, 2H, J 11.4), 1.85 (d, 2H, J12.0), 1.65-1.53 (m, 2H), 1.03 (d, 6H, J 6.4). LC-MS (m+1)=527.41

Sources & evidence

ORD record
ord-f1cdadc7fef141909d6955bbd964e2fc
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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