(R)-(+)-1-Boc-3-aminopyrrolidine → (R,E)-1-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)pyrrolidin-1-yl)-4-(dimethylamino)but-2-en-1-one

HRID 1522165Notes

Reaction equation

HRID 1522165 reaction equation
Cl[C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[N:6][C:7]=1Cl.[NH2:10][C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18]C(C)(C)C)=O)[CH2:12]1.[O:23]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[CH3:39][N:40]([CH3:47])[CH2:41]/[CH:42]=[CH:43]/C(O)=O>>[NH2:9][C:3]1[N:4]=[CH:5][N:6]=[C:7]([NH:10][C@@H:11]2[CH2:15][CH2:14][N:13]([C:16](=[O:18])/[CH:43]=[CH:42]/[CH2:41][N:40]([CH3:47])[CH3:39])[CH2:12]2)[C:2]=1[C:27]1[CH:28]=[CH:29][C:24]([O:23][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:25][CH:26]=1

Participants

5

Reactant 4

HCID 854070(R)-(+)-1-Boc-3-aminopyrrolidineHCID 27343774-Phenoxyphenylboronic acidHCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidHCID 242192625,6-Dichloro-pyrimidin-4-ylamine

Product 1

HCID 71092905(R,E)-1-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)pyrrolidin-1-yl)-4-(dimethylamino)but-2-en-1-one

Procedure

(R,E)-1-(3-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)pyrrolidin-1-yl)-4-(dimethylamino)but-2-en-1-one was prepared from 5,6-dichloropyrimidin-4-amine, (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate, (4-phenoxyphenyl)boronic acid, and (E)-4-(dimethylamino)but-2-enoic acid using methods B, C, D and E. HPLC purity: 99%. MS: m/z=459 [M+H]+.

Sources & evidence

ORD record
ord-ff80ed9863d84d2b8514b7a4bebfe968
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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