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Triethylamine → HCID 25183073, compound

HRID 1946681
Notes
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Reaction equation

HRID 1946681 reaction equation
[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([OH:16])=O)[CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1N=C(C(OC)=O)C=C(NCC2CCCC2)N=1.[NH2:39][C:40]1[CH:47]=[CH:46][C:43]([CH2:44][OH:45])=[CH:42][CH:41]=1.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[CH:1]1([N:7]([CH2:17][CH:18]2[CH2:20][CH2:19]2)[C:8]2[N:13]=[CH:12][N:11]=[C:10]([C:14]([NH:39][C:40]3[CH:47]=[CH:46][C:43]([CH2:44][OH:45])=[CH:42][CH:41]=3)=[O:16])[CH:9]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 693314-Aminobenzyl alcoholHCID 594468416-[Cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylic acid2×HCID 86644304HCID 86644304, compound

Product 1

HCID 25183073HCID 25183073, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(cyclohexyl-cyclopropylmethyl-amino)-pyrimidine-4-carboxylic acid (Intermediate 13, 1.00 g; 3.63 mmol) in dry DMF (100 ml) was treated with polymer-supported Mukaiyama reagent, prepared as described in “S. Crosignani et al. Org. Lett. 2004, 6(24), 4579-4582” (2 987 mg; 6.54 mmol), 4-aminobenzyl alcohol (Fluka, 492 mg; 3.99 mmol) and triethylamine (1.52 ml; 10.9 mmol). The reaction mixture was then stirred at room temperature for 18 hours. DCM was added and the product was filtered through an SPE column (Isolute NH2, 10 g) and the column washed with DCM. The mixture was concentrated then rediluted in AcOEt. The organic phase was washed 5 times with brine, dried over MgSO4 and the solvent removed under vacuum to give the title compound (990 mg, 72%).

Workup

  1. customprepared
  2. filtrationthe product was filtered through an SPE column (Isolute NH2, 10 g)
  3. washthe column washed with DCM
  4. concentrationThe mixture was concentrated
  5. additionthen rediluted in AcOEt
  6. washThe organic phase was washed 5 times with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-8af2e2d7fb244f2faf0994e5cc97178b
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399448B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes