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2-Mesitylenesulfonyl chloride → 2-Amino-5-(4-(3-hydroxypropoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonate

HRID 2207085
Notes
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Reaction equation

HRID 2207085 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].C(N(C(C)C)CC)(C)C.Cl.[NH2:24][C:25]1[N:30]=[C:29]([OH:31])[C:28]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][OH:43])=[CH:35][C:34]=2[O:44][CH3:45])=[C:27]([CH3:46])[N:26]=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:31][C:29]1[C:28]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH2:41][CH2:42][OH:43])=[CH:35][C:34]=2[O:44][CH3:45])=[C:27]([CH3:46])[N:26]=[C:25]([NH2:24])[N:30]=1)(=[O:11])=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178493485HCID 178493485, compound

Product 1

HCID 1179928752-Amino-5-(4-(3-hydroxypropoxy)-2-methoxybenzyl)-6-methylpyrimidin-4-yl 2,4,6-trimethylbenzenesulfonateYield 88.1%

Reagents, catalysts & solvents 2

HCID 962Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

2-Mesitylenesulfonyl chloride (2.7 g) was added to a suspension of diisopropylethylamine (4.6 mL) and the product from step (vi) (2.9 g) in THF (200 mL) and the mixture was stirred under reflux for 18 h. The resulting mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash column chromatography on amino silica gel to afford the sub-title compound (3.6 g) as a white solid; 1H NMR (300 MHz, CDCl3); 6.92 (2H, s), 6.71 (1H, d), 6.40 (1H, d), 6.32 (1H, dd), 4.70 (2H, br s), 4.07 (2H, t), 3.88-3.82 (2H, m), 3.76 (3H, s), 3.73 (2H, s), 2.57 (6H, s), 2.29 (3H, s), 2.24 (3H, s), 2.06-1.98 (2H, m); LC-MS: m/z 502.

Workup

  1. temperatureunder reflux for 18 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography on amino silica gel

Sources & evidence

ORD record
ord-adf4dd6a9f84488e84ad4c895a4a1cee
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09376398B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes