2-Aminopyrimidine-5-boronic acid, pinacol ester → 5-(6-(((2r,6s)-2,6-Dimethyl-4-(methylsulfonyl)piperazin-1-yl)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amine

HRID 1365465Notes

Reaction equation

HRID 1365465 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3[C@H:17]([CH3:18])[CH2:16][N:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:14][C@@H:13]3[CH3:23])=[C:8]([CH3:24])[C:6]=2[N:7]=1.[NH2:31][C:32]1[N:37]=[CH:36][C:35](B2OC(C)(C)C(C)(C)O2)=[CH:34][N:33]=1>>[CH3:23][C@@H:13]1[CH2:14][N:15]([S:19]([CH3:22])(=[O:21])=[O:20])[CH2:16][C@H:17]([CH3:18])[N:12]1[CH2:11][C:9]1[S:10][C:5]2[C:4]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[N:3][C:2]([C:35]3[CH:34]=[N:33][C:32]([NH2:31])=[N:37][CH:36]=3)=[N:7][C:6]=2[C:8]=1[CH3:24]

Participants

3

Reactant 2

HCID 177502122-Aminopyrimidine-5-boronic acid, pinacol esterHCID 866235702-chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

Product 1

HCID 249483535-(6-(((2r,6s)-2,6-Dimethyl-4-(methylsulfonyl)piperazin-1-yl)methyl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-2-yl)pyrimidin-2-amineYield 58.6%

Procedure

2-Chloro-6-((2S,6R)-4-methanesulfonyl-2,6-dimethyl-piperazin-1-ylmethyl)-7-methyl-4-morpholin-4-yl-thieno[3,2-d]pyrimidine (135 mg, 0.29 mmol) was reacted with 2-amino-pyrimidine-5-boronic acid pinacol ester (88 mg, 0.4 mmol) in General Procedure A. After extraction into 2M HCl, the mixture was washed with ethyl acetate then made basic and the precipitate collected by filtration. Purification using a thiourea SPE cartridge gave 420 as a cream solid (90 mg, 0.17 mmol) NMR (CDCl3, 400 MHz), 9.25 (s, 2H); 5.12 (s, 2H); 3.95 (t, 4H, J=4.6 Hz); 3.95 (s, 2H); 3.82 (t, 4H, J=4.8 Hz); 3.51 (d, 2H, J=11.3 Hz); 2.82 (m, 2H); 2.74 (s, 3H); 2.55 (t, 2H, J=10.8 Hz); 2.33 (s, 3H); 1.06 (d, 6H, J=6.3 Hz) MS: (ESI+): MH+=533.30

Workup

  1. extractionAfter extraction into 2M HCl
  2. washthe mixture was washed with ethyl acetate
  3. filtrationthe precipitate collected by filtration
  4. customPurification

Sources & evidence

ORD record
ord-e11f2894c55f420ba18dc13824eafa69
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

Loading…