4-Aminobenzoic Acid → HCID 136057403, compound

HRID 1860228Notes

Reaction equation

HRID 1860228 reaction equation
[C:1]([NH:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH:18]=O)[N:13]=2)[N:8]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[C:1]([NH:6][C:7]1[NH:16][C:15](=[O:17])[C:14]2[C:9](=[N:10][CH:11]=[C:12]([N:13]=2)[CH2:18][NH:20][C:21]2[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=2)[N:8]=1)(=[O:5])[CH:2]([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 135967978HCID 135967978, compound

Product 1

HCID 136057403HCID 136057403, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N2-iBu-6-formylpterin (25) 4.0 gm, 15 mmole) was suspended in MeOH. To this suspension was added 4-aminobenzoic acid (2.1 g, 15 mmole) followed by stirring for 10 minutes. The reaction mixture was then cooled in an ice bath with continuous stirring. A solution of pyridinium para-toluene sulfonate (PPTS, 1 M in MeOH, 15 ml, 15 mmol) was added in one portion, followed by the addition of pyridine-borane complex (1.9 ml of 8M solution, 15 mmol) dropwise over a period of 10 minutes. The ice bath was removed, and stirring was continued at room temperature for 3 hours. The fine precipitated product was collected by centrifugation and washed with a 1:1 mixture of hexanes-MeOH several times, and finally with MeOH. The product was dried in vacuum over P205 for 24 sours to give light cream-colored powder, yield=5.3 gm, 91%. 1H NMR (DMSO): δ 8.87 (s, 1H), 4.62 (s, 2H), 2.75-2.82 (m, 1H), 1.13, 1.16 (2s, 6H); MS, m/z , M-H+=383 for C18H18N6O4.

Workup

  1. temperatureThe reaction mixture was then cooled in an ice bath with continuous stirring
  2. additionfollowed by the addition of pyridine-borane complex (1.9 ml of 8M solution, 15 mmol) dropwise over a period of 10 minutes
  3. customThe ice bath was removed
  4. stirringstirring
  5. waitwas continued at room temperature for 3 hours
  6. customThe fine precipitated product was collected by centrifugation
  7. washwashed with a 1:1 mixture of hexanes-MeOH several times
  8. customThe product was dried in vacuum over P205 for 24 sours
  9. customto give light cream-colored powder, yield=5.3 gm, 91%

Sources & evidence

ORD record
ord-637bac280da44ab0b64ad727957846b6
Source dataset
uspto-grants-2003_03
Patent number
US06528631B1

Reaction notes

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