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Triethylamine → 5-{9-Isobutyl-8-[4-(methylsulfonyl)piperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

HRID 421297
Notes
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Reaction equation

HRID 421297 reaction equation
C(N(CC)CC)C.[S:8](Cl)([CH3:11])(=[O:10])=[O:9].[CH2:13]([N:17]1[C:25]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:24][C:23]2[C:18]1=[N:19][C:20]([C:38]1[CH:39]=[N:40][C:41]([NH2:44])=[N:42][CH:43]=1)=[N:21][C:22]=2[N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[CH:14]([CH3:16])[CH3:15]>CN1C(=O)CCC1>[CH2:13]([N:17]1[C:25]([N:26]2[CH2:31][CH2:30][N:29]([S:8]([CH3:11])(=[O:10])=[O:9])[CH2:28][CH2:27]2)=[N:24][C:23]2[C:18]1=[N:19][C:20]([C:38]1[CH:43]=[N:42][C:41]([NH2:44])=[N:40][CH:39]=1)=[N:21][C:22]=2[N:32]1[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1)[CH:14]([CH3:16])[CH3:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 593335015-(9-Isobutyl-6-morpholino-8-(piperazin-1-yl)-9H-purin-2-yl)pyrimidin-2-amine

Product 1

HCID 453778615-{9-Isobutyl-8-[4-(methylsulfonyl)piperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amineYield 51%

Reagents, catalysts & solvents 1

HCID 13387
N-methyl-2-pyrrolidone
Solvent

Procedure

Triethylamine (143 μl) and mesyl chloride (50 μl, 0.63 mmol) were added to 5-(9-isobutyl-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl)pyrimidin-2-amine (2 ml of solution of 100 mg of this compound in 1 ml of NMP) and the resulting mixture was stirred for 1 hour. Mesyl chloride (50 μl, 0.63 mmol) was further added, the resulting mixture was stirred for 1 hour, then the reaction mixture was partitioned with ethyl acetate and water, and the organic layer was dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid) to give the title compound (135 mg, 51%) as a pale yellow solid.

Workup

  1. stirringthe resulting mixture was stirred for 1 hour
  2. customthe reaction mixture was partitioned with ethyl acetate and water
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC (column, NOMURA Develosil Combi-RP-5; mobile phase, acetonitrile/water/formic acid)

Sources & evidence

ORD record
ord-122a053be12a49d19c490a9d3b62a4fa
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08097622B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes