Hydrochloric Acid → HCID 18617848, compound

HRID 1264224Notes

Reaction equation

HRID 1264224 reaction equation
C[O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:18][C:13]3[N:14]=[CH:15][N:16]=[CH:17][C:12]=3[CH:11]=2)=[CH:6][CH:5]=1.C1COCC1.CO.[OH-].[Na+].Cl>O>[N:14]1[C:13]2[NH:18][C:10]([C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:19])=[O:2])=[CH:9][CH:8]=3)=[CH:11][C:12]=2[CH:17]=[N:16][CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 54545751HCID 54545751, compound

Product 1

HCID 18617848HCID 18617848, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(7H-pyrrolo[2,3-d]pyrimidin-6-yl)-benzoic acid methyl ester (0.601 g, 2.4 mmol) (reference example 43a) in 1:1 THF-methanol (10 mL) is added NaOH (10N) (2.4 mL, 24 mmol) and 0.5 ml H2O. The resulting solution is stirred for 1 hour then cooled to 0°-5° C. and adjusted to pH 3 with 2N HCl. The precipitated solid is filtered off, washed with a small volume of water and dried under high vacuum to give 0.355 g of title compound as a yellow solid. 1H NMR (DMSO) δ 7.59 (s, 1H), 8.10 (d, J=8 Hz, 2H), 8.20 (d, J=8 Hz, 2H), 9.22 (s, 1H), 9.50 (bs, 1H), 14.10 (bs, 1H). MS (EI) m/z 239 (M+).

Workup

  1. temperaturethen cooled to 0°-5° C.
  2. filtrationThe precipitated solid is filtered off
  3. washwashed with a small volume of water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-37086d032f5a44e99e53298215e11521
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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