Lithium hydroxide, monohydrate → 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid

HRID 600464Notes

Reaction equation

HRID 600464 reaction equation
C([O:3][C:4]([C:6]1[C:10]2[N:11]=[CH:12][N:13]=[C:14]([Cl:15])[C:9]=2[NH:8][CH:7]=1)=[O:5])C.O[Li].O>C1COCC1.O>[Cl:15][C:14]1[C:9]2[NH:8][CH:7]=[C:6]([C:4]([OH:5])=[O:3])[C:10]=2[N:11]=[CH:12][N:13]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 52987614Ethyl 4-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate

Product 1

HCID 457897304-chloro-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-chloro-4,6-diazaindole 5 (4.0 g, 18 mmol) in THF (90 mL) was added a solution of LiOH.H2O (2.5 g, 59 mmol) in H2O (60 mL). The reaction mixture was stirred at 100° C. for 1 d, concentrated and recrystallized from H2O (20 mL). The crystals were collected by filtration, washed with H2O and dried under high vacuum. The off-white solid was shown to be the lithium salt of the diazaindole carboxylic acid 6 (quantitative), which was used without further purification. 1H NMR: (500 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.14 (s, 1H); LC/MS: (ES+) m/z (M+H)+=198; HPLC Rt=0.47 min., column G.

Workup

  1. concentrationconcentrated
  2. customrecrystallized from H2O (20 mL)
  3. filtrationThe crystals were collected by filtration
  4. washwashed with H2O
  5. customdried under high vacuum
  6. customwas used without further purification

Sources & evidence

ORD record
ord-351e816dde584e348bc1a07d757f6d11
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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