Diisopropylethylamine → HCID 86660190, compound

HRID 467723Notes

Reaction equation

HRID 467723 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]

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 8028TetrahydrofuranSolvent

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-53145e5e27674870984cd5ad706be32a
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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