Sodium Hydroxide → 2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid tert-butyl ester

HRID 1842848Notes

Reaction equation

HRID 1842848 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[N:9]=[C:10]([C:11]3[NH:12][CH2:13][CH2:14][N:15]=3)[C:3]=12.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].[OH-].[Na+]>CS(C)=O>[C:20]([O:19][C:17](=[O:18])[CH2:16][N:8]1[C:4]2=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]2[C:10]([C:11]2[NH:15][CH:14]=[CH:13][N:12]=2)=[N:9]1)([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 59242681tert-butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate

Product 1

HCID 1360797532-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid tert-butyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of tert-Butyl 2-(4-amino-3-(4,5-dihydro-1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetate (84 g, 0.265 mol) and DMSO (900 mL) in an ice water bath was added Dess-Martin periodinane (169.6 g, 0.4 mol) in portions while keeping the internal temperature below 25° C. The mixture was stirred for 2 h at room temperature and then poured into ice water (2 L) which contained 84 g of Na2S2O3. The mixture was adjusted to pH 12-14 with 3 N NaOH and filtered to give a solid, which was washed with water, re-suspended in ice-water (2 L), filtered, washed with water (500 mL), EtOAc (100 mL×2) and Et2O (100 mL×2), and dried in vacuo to give (2-(4-amino-3-(1H-imidazol-2-yl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)acetic acid tert-butyl ester (66.2 g, 80% yield). MS (ES) m/z 316.1 (M+H+).

Workup

  1. customthe internal temperature below 25° C
  2. filtrationfiltered
  3. customto give a solid, which
  4. washwas washed with water
  5. filtrationfiltered
  6. washwashed with water (500 mL), EtOAc (100 mL×2) and Et2O (100 mL×2)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-9570f4131d694aa58f39c8c447f7b41b
Source dataset
uspto-grants-2015_02
Patent number
US08946240B2

Reaction notes

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