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

HRID 1095469Notes

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

Reactant 4

HCID 284Formic Acid

HCID 962Water

HCID 7918Acetic Anhydride

HCID 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 1 h. The reaction mixture was then warmed to 100° C. and stirred for 16 h. The reaction mixture was cooled and water was added (40 mL). The precipitated was filtered and washed thoroughly with water and hexanes to give 5,6-diphenylfuro[2,3-d]pyrimidin-4(3H)-one (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

temperatureThe reaction mixture was then warmed to 100° C.
stirringstirred for 16 h
temperatureThe reaction mixture was cooled
filtrationThe precipitated was filtered
washwashed thoroughly with water and hexanes

Sources & evidence

ORD record: ord-d97fe41ce9a14a0cb4e93698fbd508ae
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138194B2

Reaction notes

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