Acetic Acid → HCID 90408675, compound

HRID 2177617Notes

Reaction equation

HRID 2177617 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[C:10](C)=[N:11][CH:12]=[CH:13][C:14]=2N)=[N:6][CH:7]=1.[CH3:17][C:18](O)=O.[N:21](OC(C)(C)C)=O>C1COCC1>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[C:9]3[CH:14]=[CH:13][N:21]=[C:18]([CH3:17])[C:10]=3[N:11]=[CH:12]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10906Tert-Butyl nitriteHCID 90408762HCID 90408762, compound

Product 1

HCID 90408675HCID 90408675, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-(5-fluoropyrimidin-2-yl)-2-methylpyridine-3,4-diamine (0.50 g, 2.28 mmol) in THF (15 ml) and HOAc (0.14 ml, 2.51 mmol) was treated with t-butyl nitrite (0.45 ml, 3.42 mmol) and heated to 100° C. for 90 min. The reaction was concentrated, diluted with 1N NaHCO3, and extracted with DCM (50 mL×3). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2; EtOAc:Hex) gave the title compound (0.40 g, 77%). MS (ESI): mass calcd. for C10H7FN6, 230.07. m/z found, 231.1 [M+H]+.

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with 1N NaHCO3
  3. extractionextracted with DCM (50 mL×3)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8039a20a25544e0fa8f2751e1354a6f4
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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