Trimethyl orthoformate → 5-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

HRID 1365807Notes

Reaction equation

HRID 1365807 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.Cl.[CH3:20][S:21]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].C([O-])(=O)C.[Na+].COC(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([CH2:11][N:27]3[CH2:28][CH2:29][N:24]([S:21]([CH3:20])(=[O:23])=[O:22])[CH2:25][CH2:26]3)[S:8][C:6]=2[N:7]=1

Participants

7

Reactant 5

HCID 9005Trimethyl orthoformateHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 162656121-Methanesulfonylpiperazine hydrochlorideHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Product 1

HCID 445416755-Chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

5-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde was dissolved in dichloroethane with 1-methylsulfonylpiperazine hydrochloride (1.45 eq), sodium acetate (1.45 eq), and trimethylorthoformate (1.45 eq). The solution was stirred overnight. Sodium triacetoxyborohydride (1.35 eq) was added and after three hours at room temperature the reaction was quenched with saturated sodium bicarbonate solution. The aqueous was extracted with methylene chloride, dried with sodium sulfate and purified by silica gel chromatography to give 5-chloro-2-((4-methylsulfonylpiperazin-1-yl)methyl)-7-morpholinothiazolo[5,4-d]pyrimidine.

Workup

  1. customwas quenched with saturated sodium bicarbonate solution
  2. extractionThe aqueous was extracted with methylene chloride
  3. dry with materialdried with sodium sulfate
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-87c4a8662d8f439482d1fe507cecbb26
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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