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 391147Notes

Reaction equation

HRID 391147 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 86623570HCID 86623570, compound

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-36307dab7d0d403c8912f4b9dcff1374
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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