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Diisopropylethylamine → HCID 86660190, compound

HRID 2368320
Notes
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Reaction equation

HRID 2368320 reaction equation
[NH2:1][C:2]1[C:3]([C:8]([OH:10])=O)=[N:4][CH:5]=[N:6][CH:7]=1.[NH2:11][CH2:12][C:13]([CH3:16])([OH:15])[CH3:14].C(N(C(C)C)C(C)C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C1COCC1>[OH:15][C:13]([CH3:16])([CH3:14])[CH2:12][NH:11][C:8]([C:3]1[C:2]([NH2:1])=[CH:7][N:6]=[CH:5][N:4]=1)=[O:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 111923Propylphosphonic anhydrideHCID 122589125-Aminopyrimidine-4-carboxylic acid

Product 1

HCID 86660190HCID 86660190, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a stirred mixture of 5-aminopyrimidine-4-carboxylic acid (200 mg, 1.44 mmol) and 1-amino-2-methylpropan-2-ol (128 mg, 1.44 mmol) at rt in THF (5 ml) under an argon atmosphere were added N-ethyldiisoproplyamine (743 mg, 978 μl, 5.75 mmol) and 1-propanephosphonic acid cyclic anhydride (2.29 g, 2.16 ml, 3.59 mmol). The mixture was stirred at rt for 21 hrs, then concentrated. The crude product was purified by column chromatography with EtOAc/MeOH as eluent providing the title compound (216 mg, 72%) as off-white solid.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography with EtOAc/MeOH as eluent

Sources & evidence

ORD record
ord-b6011126272c4141a351e13c659aa1d8
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08703768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes