Formic Acid → 5,6-Diphenylfuro[2,3-d]pyrimidin-4-ol

HRID 1891030Notes

Reaction equation

HRID 1891030 reaction equation
[NH2:1][C:2]1[O:3][C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]=1[C:7]#[N:8].[CH:21](O)=O.C(OC(=O)C)(=O)C.[OH2:31]>>[C:9]1([C:5]2[C:6]3[C:2](=[O:3])[NH:1][CH:21]=[N:8][C:7]=3[O:31][C:4]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 3896992-Amino-4,5-diphenyl-3-furonitrile

Product 1

HCID 112431895,6-Diphenylfuro[2,3-d]pyrimidin-4-olYield 95%

Conditions

Temperature
0 °C

Procedure

A mixture of 2-amino-4,5-diphenylfuran-3-carbonitrile (2.0 g) and formic acid (24 mL) was cooled to 0° C. and acetic anhydride (24 mL) was added dropwise. The resulting mixture was stirred for another 1 h and was then heated at 100° C. for 16 h. The reaction mixture was cooled and water was added (40 mL). The precipitate was collected by filtration and washed thoroughly with water and hexanes to give the title compound (2.1 g, 95%). 1H NMR (300 MHz, CDCl3): δ 7.94 (s, 1H), 7.56-7.52 (m, 4H), 7.46-7.43 (m, 3H), 7.32-7.28 (m, 3H), 7.22 (s, 1H). LC-MS (ESI) m/z 289.1 (M+H).

Workup

  1. temperaturewas then heated at 100° C. for 16 h
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was collected by filtration
  4. washwashed thoroughly with water and hexanes

Sources & evidence

ORD record
ord-6866de4177d74829b21009d65db99d1f
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Reaction notes

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