HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

N,N,N',N'-Tetramethyl-1,3-diaminopropane → 2-Amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 2207090
Notes
Print preview

Reaction equation

HRID 2207090 reaction equation
[C:1]1([CH3:13])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9](Cl)(=[O:11])=[O:10].CN(C)CCCN(C)C.[NH2:23][C:24]1[N:29]=[C:28]([OH:30])[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:48])[CH3:47])([CH3:45])[CH3:44])=[CH:34][C:33]=2[O:50][CH3:51])=[C:26]([CH3:52])[N:25]=1>C1COCC1.O>[CH3:13][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[S:9]([O:30][C:28]1[C:27]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][O:42][Si:43]([C:46]([CH3:49])([CH3:47])[CH3:48])([CH3:44])[CH3:45])=[CH:34][C:33]=2[O:50][CH3:51])=[C:26]([CH3:52])[N:25]=[C:24]([NH2:23])[N:29]=1)(=[O:11])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8084N,N,N',N'-Tetramethyl-1,3-diaminopropaneHCID 130462-Mesitylenesulfonyl chlorideHCID 1784934872-amino-5-[[4-[3-[tert-butyl(dimethyl)silyl]oxypropoxy]-2-methoxyphenyl]methyl]-6-methyl-1H-pyrimidin-4-one

Product 1

HCID 871670752-Amino-5-(4-(3-(tert-butyldimethylsilyloxy)propoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonateYield 95.4%

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-Mesitylenesulfonyl chloride (4.96 g, 22.7 mmol) was added to a solution of N,N,N′,N′-tetramethyl-1,3-propanediamine (3.79 mL, 22.7 mmol) and the product of example 8 step (v) (6.55 g, 15.1 mmol) in THF (66 mL) and the mixture was stirred at RT for 3 h. The resulting mixture was diluted with water and extracted with EtOAc. And the combined organic solutions were washed with brine, dried and concentrated. The residue was purified via chromatography on silica to give 8.87 g of the subtitle compound as a white solid; 1H NMR (CDCl3); 6.93 (2H, s), 6.71 (1H, d), 6.41 (1H, d), 6.33 (1H, dd), 4.66 (2H, br s), 4.02 (2H, t), 3.78 (3H, s), 3.77-3.82 (2H, m), 3.75 (2H, s), 2.59 (6H, s), 2.31 (3H, s), 2.25 (3H, s), 1.93-2.01 (2H, m), 0.89 (9H, s), 0.05 (6H, s); LC-MS: m/z 616.

Workup

  1. extractionextracted with EtOAc
  2. washAnd the combined organic solutions were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via chromatography on silica

Sources & evidence

ORD record
ord-b919020b0a50457e92fec837cce461a2
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376398B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes