Sodium Hydroxide → HCID 69959031, compound

HRID 1532970Notes

Reaction equation

HRID 1532970 reaction equation
[ClH:1].C[O:3][C:4](=[O:38])[CH2:5][NH:6][CH2:7][C:8]1[O:9][C:10]([C:13]2[N:37]=[CH:36][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:24][CH:23]=4)[C:15]=3[CH:14]=2)=[CH:11][CH:12]=1.[OH-].[Na+]>CC(C)=O>[ClH:1].[CH2:29]([O:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:20]2[C:15]3[CH:14]=[C:13]([C:10]4[O:9][C:8]([CH2:7][NH:6][CH2:5][C:4]([OH:38])=[O:3])=[CH:12][CH:11]=4)[N:37]=[CH:36][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:23][CH:24]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69959093HCID 69959093, compound

Product 1

HCID 69959031HCID 69959031, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

((5-(4-(4-Benzyloxy-phenylamino)-pyrido[3,4-d]pyrimidin-6-yl)-furan-2-ylmethyl)-amino)acetic acid methyl ester hydrochloride (0.04 g) was suspended in acetone (5 ml) and 2N sodium hydroxide solution (5 ml) added. The resulting solution was stirred at room temperature for 30 mins. The acetone was removed under vacuum and the solution acidified with 2N HCl. The mixture was chilled in an ice-bath and the precipitate filtered off and washed with a little cold water and then acetone. The residue was dried at 60° C. under vacuum to give the product as an orange solid (0.03 g); δH [2H6]-DMSO 10.30 (1H, b), 9.10 (1H, s), 8.71 (11H, s), 8.59 (11H, s), 7.75 (2H, d), 7.53−7.28 (5H, m), 7.15−7.00 (3H, m), 6.62 (1H, d), 5.12 (2H, s), 4.07 (2H, s); m/z 482 (M+1)+.

Workup

  1. customThe acetone was removed under vacuum
  2. temperatureThe mixture was chilled in an ice-bath
  3. filtrationthe precipitate filtered off
  4. washwashed with a little cold water
  5. customThe residue was dried at 60° C. under vacuum

Sources & evidence

ORD record
ord-04b3608f81404845af0e3ad699a37e5a
Source dataset
uspto-grants-2001_03
Patent number
US06207669B1

Reaction notes

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