Water → [1-Methyl-4-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-alpha]phthalazine-6-yl]oxy}methyl)-1H-[1,2,3]triazol-5-yl]methanol

HRID 2183519Notes

Reaction equation

HRID 2183519 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CC([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:24][CH2:25][C:26]1[N:30]([CH3:31])[N:29]=[N:28][C:27]=1[CH2:32][O:33][C:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[C:37]2=[N:44][N:45]=[C:46]([C:47]3[CH:51]=[C:50]([CH3:52])[O:49][N:48]=3)[N:36]2[N:35]=1)(C)C.O>C1COCC1.CO>[CH3:31][N:30]1[C:26]([CH2:25][OH:24])=[C:27]([CH2:32][O:33][C:34]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]3=[N:44][N:45]=[C:46]([C:47]4[CH:51]=[C:50]([CH3:52])[O:49][N:48]=4)[N:36]3[N:35]=2)[N:28]=[N:29]1

Participants

6

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 1317249446-({[5-({[(1,1-Dimethylethyl)(diphenyl)silyl]oxyl}methyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-alpha]phthalazine

Product 1

HCID 131724945[1-Methyl-4-({[3-(5-methylisoxazol-3-yl)[1,2,4]triazolo[3,4-alpha]phthalazine-6-yl]oxy}methyl)-1H-[1,2,3]triazol-5-yl]methanolYield 56%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tetrabutylammonium fluoride (3.3 mmol) in THF (1.0 M, 3.3 ml) was added to a stirred solution of 6-({[5-({[(1,1-dimethylethyl)(diphenyl)silyl]oxy}methyl)-1-methyl-1H-[1,2,3]triazol-4-yl]methyl}oxy)-3-(5-methylisoxazol-3-yl)-[1,2,4]triazolo[3,4-α]phthalazine (1.90 g, 3.3 mmol) in THF (50 ml) and MeOH (10 ml) at room temperature under N2 and the reaction mixture was stirred overnight. H2O (10 ml) was added and then the mixture was concentrated under reduced pressure to remove the organic solvents. The resulting solid was filtered off, washed with H2O (20 ml), then triturated with CH2Cl2 (100 ml), filtered and dried, to yield the desired hydroxymethyltriazole (672 mg, 56%). 1H NMR (400 MHz, d6-DMSO) δ 8.56 (1H, d, J=7.9 Hz), 8.17-8.04 (2H, m), 7.91 (1H, td, J=7.9, 0.9 Hz), 7.22 (1H, s), 5.71 (2H, s), 5.42 (1H, t, J=5.6 Hz), 4.72 (2H, d, J=5.6 Hz), 4.06 (3H, s), 2.59 (3H, s).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customto remove the organic solvents
  3. filtrationThe resulting solid was filtered off
  4. washwashed with H2O (20 ml)
  5. customtriturated with CH2Cl2 (100 ml)
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-501ceeeb29d1478a91dc502eb73df3db
Source dataset
uspto-grants-2005_05
Patent number
US06900209B2

Reaction notes

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