Sodium hydride → 2-Amino-4-(cyclopropylmethyloxy)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidine

HRID 1517434Notes

Reaction equation

HRID 1517434 reaction equation
C([NH:4][C:5]1[N:6]=[C:7](C2N=CNN=2)[C:8]2[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)(=O)C.[H-].[Na+].[CH:29]1([CH2:32][OH:33])[CH2:31][CH2:30]1>O1CCOCC1>[NH2:4][C:5]1[N:6]=[C:7]([O:33][CH2:32][CH:29]2[CH2:31][CH2:30]2)[C:8]2[N:14]=[C:13]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 178474430HCID 178474430, compound

Product 1

HCID 591992052-Amino-4-(cyclopropylmethyloxy)-6-(4-fluorophenyl)pyrido[3,2-d]pyrimidineYield 47%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-acetamido-4-(1,2,4-triazolyl)-6-(4-fluorophenyl)-pyrido[3,2-d]pyrimidine (52 mg, 0.15 mmol) in cyclopropylmethanol (1 ml) and dioxane (3 ml) was added NaH (60% dispersion in mineral oil, 0.25 mmol, 15 mg). The reaction mixture was stirred overnight at room temperature. The solvents were evaporated in vacuo, and the residue was purified by preparative TLC, the mobile phase being a methanol/dichloromethane mixture in a ratio of 10:90, yielding the pure title compound (22 mg, yield: 47%) which was characterised as follows: MS (m/z): 311 ([M+H]+, 100).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-95c4a1b41f8146348e4e9172e5d932c9
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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