4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)aniline

HRID 1626563Notes

Reaction equation

HRID 1626563 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.Cl[C:18]1[N:19]=[C:20]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]2[CH3:34])[C:21]2[CH2:26][N:25]([CH3:27])[CH2:24][C:22]=2[N:23]=1>>[CH3:27][N:25]1[CH2:26][C:21]2[C:20]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][C@@H:29]3[CH3:34])=[N:19][C:18]([C:9]3[CH:10]=[CH:11][C:12]([NH2:13])=[CH:14][CH:15]=3)=[N:23][C:22]=2[CH2:24]1

Participants

3

Reactant 2

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 86663154(S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 66679184(S)-4-(6-methyl-4-(3-methylmorpholino)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-2-yl)anilineYield 72%

Procedure

Step 2 Method as intermediate 5, using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline and (S)-4-(2-chloro-6-methyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine. The crude reaction mixture was partitioned between water and EtOAc, the phases separated and the organic layer dried over magnesium sulphate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (0-15% MeOH/DCM), to yield a pale yellow oil (477 mg, 72%).

Workup

  1. customThe crude reaction mixture
  2. customwas partitioned between water and EtOAc
  3. customthe phases separated
  4. dry with materialthe organic layer dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by flash chromatography (0-15% MeOH/DCM)

Sources & evidence

ORD record
ord-8c583214915f4e56ba41cd6ec8daaa43
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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