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Hydrochloric Acid → N-(2-(Benzylthio)-6-{[(2R)-2-hydroxypropyl]amino}pyrimidin-4-yl)methanesulfonamide

HRID 424659
Notes
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Reaction equation

HRID 424659 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[C:11]([NH:20][CH2:21][CH2:22][OH:23])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N[CH2:25][C@H](O)C.CCOC(C)=O.Cl>CN1C(=O)CCC1.O>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])[CH:12]=[C:11]([NH:20][CH2:21][C@H:22]([OH:23])[CH3:25])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 439938(2R)-1-aminopropan-2-olHCID 57833129N-{2-(Benzylthio)-6-[(2-hydroxyethyl)amino]pyrimidin-4-yl}methanesulfonamide

Product 1

HCID 57833173N-(2-(Benzylthio)-6-{[(2R)-2-hydroxypropyl]amino}pyrimidin-4-yl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To the subtitle product of Example 19 step (0.20 g) in NMP (2 ml) was added (2R)-1-amino-2-propanol (0.46 g) and the reaction was heated at 80° C. for 6 h. To the reaction was added EtOAc (50 ml) and H2O (20 ml). This solution was acidified with aqueous hydrochloric acid. The organic layer separated and washed with H2O (2×20 ml), brine (20 ml) and the organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give a solid. This material was purified by reverse phase HPLC (90% to 5% 0.02 M ammonium hydroxide/acetonitrile) to yield the title compound as a solid. Yield: 20 mg.

Workup

  1. customThe organic layer separated
  2. washwashed with H2O (2×20 ml), brine (20 ml)
  3. dry with materialthe organic layer was dried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. customto give a solid
  6. customThis material was purified by reverse phase HPLC (90% to 5% 0.02 M ammonium hydroxide/acetonitrile)

Sources & evidence

ORD record
ord-abdd0552c51b4ffaa8bf169cdc859f77
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106063B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes