1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → HCID 12472439, compound

HRID 556422Notes

Reaction equation

HRID 556422 reaction equation
[O:1]=[C:2]1[NH:7][C:6](=[O:8])[C:5]([NH:9]/[C:10](=[CH:15]/[C:16]([O:18]C)=O)/[C:11]([O:13][CH3:14])=[O:12])=[CH:4][NH:3]1.C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>>[O:1]=[C:2]1[NH:3][C:4]2[C:16](=[O:18])[CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[NH:9][C:5]=2[C:6](=[O:8])[NH:7]1

Participants

3

Reactant 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 12285744HCID 12285744, compound2×

Product 1

HCID 12472439HCID 12472439, compoundYield 63.3%

Conditions

Temperature
220 °C

Procedure

In a 2 liter-4 neck flask fitted with a reflux condenser was placed dimethyl (2E)-2-[(2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)amino]-2-butenedioate (Intermediate 1.1) (38.5 g; 0.14 mol; 1 eq.) dowtherm(R) A (1 L)(phenyl ether-biphenyl eutectic). The suspension was stirred with a mechanical stirrer under argon and heated to 220° C. The reaction was monitored by HPLC/LC/MS. After 3 hours the reaction was stopped by cooling followed by the addition of 300 mL of petroleum ether. The resulting precipitate was filtered and washed with DMF (2×100 mL). Methyl 2,4,8-trioxo-1,2,3,4,5,8 hexahydropyrido[3,2-d]pyrimidine-6-carboxylate (21.02 g; 62%) (Intermediate 1.2) was isolated as a yellow powder in 100% HPLC purity.

Workup

  1. customIn a 2 liter-4 neck flask fitted with a reflux condenser
  2. temperatureby cooling
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with DMF (2×100 mL)

Sources & evidence

ORD record
ord-edca38d78ee743fcb0a34e5cf5c40fa5
Source dataset
uspto-grants-2011_11
Patent number
US08058289B2

Reaction notes

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