N,N-Dimethylaniline → 4-Bromo-5,6-diphenyl-furo[2,3-d]pyrimidine

HRID 502651Notes

Reaction equation

HRID 502651 reaction equation
[C:1]1([C:7]2[C:15]3[C:14](O)=[N:13][CH:12]=[N:11][C:10]=3[O:9][C:8]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C1C=CC=CC=1.P(Br)(Br)[Br:33]>>[Br:33][C:14]1[C:15]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:8]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:9][C:10]=2[N:11]=[CH:12][N:13]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24614Phosphorus tribromideHCID 178518062HCID 178518062, compound

Product 1

HCID 586033114-Bromo-5,6-diphenyl-furo[2,3-d]pyrimidine

Conditions

Temperature
120 °C

Procedure

A mixture of 68 (8.2 g, 0.028 mol), phosphorous tribromide (80 mL) and N,N-dimethylaniline (5 mL) was heated to 120° C. for 3 h. After cooling, the reaction mixture was carefully poured into ice, extracted with EtOAc, and purified by silica gel column chromatography, providing 69(2.5 g) as a yellow solid. MS: 349.1, 351.1 (M+1). 1HNMR (DMSO-d6) ppm 8.82 (s, 1H), 7.55-7.41 (m, 10H).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was carefully poured into ice
  3. extractionextracted with EtOAc
  4. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-e307716b582547f5b7445b914f904e88
Source dataset
uspto-grants-2010_08
Patent number
US07776867B2

Reaction notes

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