Lithium hydroxide, monohydrate → 10-[3-(Hydroxymethyl)-4-{6-methoxy-5-[(2-methylpyrimidin-4-yl)amino]pyridin-3-yl}pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-one

HRID 592911Notes

Reaction equation

HRID 592911 reaction equation
C([O:4][CH2:5][C:6]1[C:7]([N:28]2[CH2:39][CH2:38][N:37]3[C:30](=[CH:31][C:32]4[CH2:33][C:34]([CH3:41])([CH3:40])[CH2:35][C:36]=43)[C:29]2=[O:42])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:13]=[N:14][C:15]([O:26][CH3:27])=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[N:20]=2)[CH:17]=1)(=O)C.O.[OH-].[Li+]>C(O)(C)C.C1COCC1.O>[OH:4][CH2:5][C:6]1[C:7]([N:28]2[CH2:39][CH2:38][N:37]3[C:30](=[CH:31][C:32]4[CH2:33][C:34]([CH3:40])([CH3:41])[CH2:35][C:36]=43)[C:29]2=[O:42])=[N:8][CH:9]=[CH:10][C:11]=1[C:12]1[CH:13]=[N:14][C:15]([O:26][CH3:27])=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([CH3:25])[N:20]=2)[CH:17]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86684412(2-{4,4-Dimethyl-9-oxo-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-10-yl}-4-{6-methoxy-5-[(2-methylpyrimidin-4-yl)amino]pyridin-3-yl}pyridin-3-yl)methyl Acetate

Product 1

HCID 8668441310-[3-(Hydroxymethyl)-4-{6-methoxy-5-[(2-methylpyrimidin-4-yl)amino]pyridin-3-yl}pyridin-2-yl]-4,4-dimethyl-1,10-diazatricyclo[6.4.0.02,6]dodeca-2(6),7-dien-9-oneYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

A mixture 222b (283.5 mg, 0.50 mmol) and lithium hydroxide monohydrate (630 mg, 15.0 mmol) in i-propanol/THF (1:1, 10 mL) and water (2.5 mL) was stirred at 35° C. for 0.5 h. The mixture was evaporated in vacuo and the residue was diluted with water (3 mL). It was then extracted with dichloromethane (3×20 mL). The combined organic extract was concentrated under reduced pressure to afford 222c (240 mg, 92%) as a white solid. MS-ESI: [M+H]+ 526.2

Workup

  1. customThe mixture was evaporated in vacuo
  2. additionthe residue was diluted with water (3 mL)
  3. extractionIt was then extracted with dichloromethane (3×20 mL)
  4. extractionThe combined organic extract
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-74ed8e39f3984da2b7f12cab903910df
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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