3-(Dimethylamino)pyrrolidine → HCID 58234017, compound

HRID 1365369Notes

Reaction equation

HRID 1365369 reaction equation
ClC1N=C(N2CCOCC2)C2SC(C=O)=CC=2N=1.CN(C1CNCC1)C.Cl[C:28]1[N:29]=[C:30]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[C:31]2[S:36][C:35]([CH2:37][N:38]([CH3:45])[CH:39]3[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40]3)=[CH:34][C:32]=2[N:33]=1.CC1(C)C(C)(C)OB([C:60]2[CH:61]=[N:62][C:63]([NH2:66])=[N:64][CH:65]=2)O1>>[CH3:45][N:38]([CH2:37][C:35]1[S:36][C:31]2[C:30]([N:46]3[CH2:51][CH2:50][O:49][CH2:48][CH2:47]3)=[N:29][C:28]([C:60]3[CH:61]=[N:62][C:63]([NH2:66])=[N:64][CH:65]=3)=[N:33][C:32]=2[CH:34]=1)[CH:39]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40]1

Participants

5

Reactant 4

HCID 27585193-(Dimethylamino)pyrrolidineHCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehydeHCID 86623555HCID 86623555, compound

Product 1

HCID 58234017HCID 58234017, compoundYield 14%

Procedure

2-Chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carboxaldehyde 10 was reacted with N,N-dimethyl-3-aminopyrrolidine using standard reductive amination conditions. The resulting crude oil (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-methyl-(1-methyl-pyrrolidin-3-yl)-amine was reacted with 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrimidin-2-ylamine according to General Procedure A. The resulting solid was purified by mass directed chromatography (14% yield) to give 338. NMR (CDCl3, 400 MHz), 1.83-1.90 (1H, m), 2.06-2.12 (1H, m), 2.30 (3H, s), 2.31 (3H, s), 2.57-2.62 (2H, m), 2.58-2.65 (1H, m), 2.72 (1H, t, J=9.2), 3.30-3.35 (1H, m), 3.80-3.88 (2H, m), 3.88-3.94 (4H, m), 4.03-4.09 (4H, m), 5.22 (2H, br s), 7.28 (1H, s), 9.30 (2H, s). MS: (ESI+): MH+=441

Workup

  1. customThe resulting solid was purified by mass

Sources & evidence

ORD record
ord-01ebdb303175401ba129b16928070cc5
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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