p-Phenylenediacetic acid → {4-[2-({3-[2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl}amino)-2-oxoethyl]phenyl}acetic acid

HRID 2387822Notes

Reaction equation

HRID 2387822 reaction equation
C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC.[NH2:19][CH2:20][CH2:21][CH2:22][C:23]1[C:24]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])=[N:25][C:26]([NH2:30])=[N:27][C:28]=1[CH3:29].[C:37]1([CH2:47][C:48](O)=[O:49])[CH:42]=[CH:41][C:40]([CH2:43][C:44]([OH:46])=[O:45])=[CH:39][CH:38]=1>C1COCC1.CCOC(C)=O>[NH2:30][C:26]1[N:27]=[C:28]([CH3:29])[C:23]([CH2:22][CH2:21][CH2:20][NH:19][C:48](=[O:49])[CH2:47][C:37]2[CH:42]=[CH:41][C:40]([CH2:43][C:44]([OH:46])=[O:45])=[CH:39][CH:38]=2)=[C:24]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[N:25]=1

Participants

6

Reactant 3

HCID 81760p-Phenylenediacetic acidHCID 111923Propylphosphonic anhydrideHCID 98378705-(3-Aminopropyl)-6-methyl-N4-pentylpyrimidine-2,4-diamine

Product 1

HCID 68415389{4-[2-({3-[2-Amino-4-methyl-6-(pentylamino)pyrimidin-5-yl]propyl}amino)-2-oxoethyl]phenyl}acetic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of T3P (1.591 ml, 1.57M in THF) was added to a mixture of the product from example 1 step (v) (0.2 g), TEA (0.333 ml) and 2,2′-(1,4-phenylene)diacetic acid (0.463 g) in THF (15 mL) and the mixture stirred at rt overnight. The reaction was diluted with EtOAc, washed with water, dried and evaporated under reduced pressure. Used crude in next step.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c0af51a2ae3f48da8688bd4f9de09902
Source dataset
uspto-grants-2012_09
Patent number
US08268990B2

Reaction notes

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