2-Butynoic acid → HCID 71092935, compound

HRID 1522144Notes

Reaction equation

HRID 1522144 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[OH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=O)[CH2:14][CH2:13]1.[O:25]([C:32]1[CH:37]=[CH:36][C:35](B(O)O)=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:41](O)(=O)[C:42]#[C:43]C>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([C:18](=[O:20])/[CH:41]=[CH:42]\[CH3:43])[CH2:16][CH2:17]2)[C:2]=1[C:29]1[CH:30]=[CH:31][C:26]([O:25][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 685352-Butynoic acidHCID 27343774-Phenoxyphenylboronic acidHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71092935HCID 71092935, compound

Reagents, catalysts & solvents 1

HCID 131709914Lindlars catalystCatalyst

Procedure

(Z)-1-(4-(((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)oxy)methyl)piperidin-1-yl)but-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and but-2-ynoic acid using methods A, C, D, E, and hydrogenation using Lindlar's catalyst. HPLC purity: 100%. MS: m/z=445 [M+H]+.

Sources & evidence

ORD record
ord-4f8589c6d9214ccdbed0358b48c83e89
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

Loading…