Dimethylbarbituric acid → HCID 69038971, compound

HRID 1869269Notes

Reaction equation

HRID 1869269 reaction equation
C([N:4]([CH2:8][C:9]1[S:13][C:12]([S:14]([NH:17][CH:18]([CH2:22][CH2:23][NH:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=2)[C:19]([NH2:21])=[O:20])(=[O:16])=[O:15])=[CH:11][CH:10]=1)CC=C)C=C.CN1C(=O)CC(=O)N(C)C1=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:4][CH2:8][C:9]1[S:13][C:12]([S:14]([NH:17][CH:18]([CH2:22][CH2:23][NH:24][C:25]2[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=2)[C:19]([NH2:21])=[O:20])(=[O:16])=[O:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 69038391HCID 69038391, compound

Product 1

HCID 69038971HCID 69038971, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of the bisallylamine 2c (7.25 mmol), N,N′-dimethylbarbituric acid (NDMBA 2.8 g, 18.1 mmol), and Pd(PPh3)4 (148.8 mg, 0.13 mmol) in CH3Cl2 is degassed by bubbling argon for 10 min. The reaction mixture for 3 h at r.t. whereupon the desired amine 2d precipitates as its NDMBA salt. The mixture is diluted with EtOAc (200 ml) and hexane (200 ml) and washed with water (3×50 ml). The crude compound 2D is pure enough to be used in the next step without further purification.

Workup

  1. customby bubbling argon for 10 min
  2. customThe reaction mixture for 3 h at r.t. whereupon the desired amine 2d precipitates as its NDMBA salt
  3. additionThe mixture is diluted with EtOAc (200 ml) and hexane (200 ml)
  4. washwashed with water (3×50 ml)
  5. customto be used in the next step without further purification

Sources & evidence

ORD record
ord-b5e650926a4f4d148919d6ee5dfea1ce
Source dataset
uspto-grants-2009_12
Patent number
US07638538B1

Reaction notes

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