4-Amino-5-pyrimidinecarboxamide → HCID 135923522, compound

HRID 2076817

Reaction equation

HRID 2076817 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[CH:6][N:5]=[CH:4][N:3]=1.CO[C:13](=O)[CH2:14][O:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:24][C:20]1[CH:19]=[C:18]([CH2:17][CH2:16][O:15][CH2:14][C:13]2[NH:10][C:8](=[O:9])[C:7]3[C:2]([N:1]=2)=[N:3][CH:4]=[N:5][CH:6]=3)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8182124-Amino-5-pyrimidinecarboxamideHCID 2733832Lithium HexamethyldisilazideHCID 67099252HCID 67099252, compound

Product 1

HCID 135923522HCID 135923522, compoundYield 1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of the commercially available 4-amino-5-pyrimidinecarboxamide [4786-51-0] (150 mg, 1.09 mmol) and of [2-(3-fluoro-phenyl)-ethoxy]-acetic acid methyl ester (254 mg, 1.19 mmol) in THF (7 ml) was treated with LiHMDS (1M solution in THF, 2.17 ml) and stirred overnight at ambient temperature. The resulting yellow suspension was filtered and the filtrate was evaporated to dryness and triturated with EtOAc/MeOH 9:1. The yellow solid was filtered off, the mother-liquid was evaporated and the remaining residue was purified by column chromatography (silica gel, EtOAc/MeOH, 9:1) to give the title compound as a white solid (3 mg, 1%), MS: m/e=301.1 [M+H+].

Workup

  1. filtrationThe resulting yellow suspension was filtered
  2. customthe filtrate was evaporated to dryness
  3. customtriturated with EtOAc/MeOH 9:1
  4. filtrationThe yellow solid was filtered off
  5. customthe mother-liquid was evaporated
  6. customthe remaining residue was purified by column chromatography (silica gel, EtOAc/MeOH, 9:1)

Sources & evidence

ORD record
ord-774e415be8b145c5b0dc18578322c24b
Source dataset
uspto-grants-2011_04
Patent number
US07928106B2

Linked notes

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