Sodium Hydroxide → HCID 68569057, compound

HRID 1990923Notes

Reaction equation

HRID 1990923 reaction equation
[OH-].[Na+].[C:3]([NH:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[N:22](S(C3C=CC=CC=3)(=O)=O)[C:12]=2[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1)(=[O:5])[CH3:4]>CO>[C:3]([NH:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[CH:24]=[C:23]([C:25]([OH:27])=[O:26])[NH:22][C:12]=2[N:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:15]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68568374HCID 68568374, compound

Product 1

HCID 68569057HCID 68569057, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of sodium hydroxide in methanol (65 mL, 5M, 325 mmol) is added to a solution of the pyrrolopyrimidine 28a (6.3 g, 13.1 mmol) in methanol (35 mL). After 1.5 h, MeOH is evaporated. The residue is dissolved in 2N NaOH (200 mL) and extracted with Et2O (2×30 mL). The aqueous layer is acidified to pH≈3-4 with aq. HCl (first with 12N HCl until some solid has precipitated, then with 2N HCl until pH 3-4 is reached and no more solid precipitates). The beige solid is filtered off and dried, giving 4.345 g (12.8 mmol, 98% yield) of 30a. LC/MS analysis of this material: 95% of 30a, 3% of desacetyl-30a. This material is used without further purification. 1H-NMR (D6-DMSO): δ=1.81 (s, 3H), 3.3 (m, 2H; hidden under water peak), 3.62 (m, 2H), 7.29 (s, 1H), 7.44-7.50 (m, 3H), 8.0-8.1 (brm, 2H, NH), 8.40-8.45 (m, 2H). 1H NMR (CDCl3/CD3OD, 200 MHz): δ=1.82 (s, 3H), 3.53 (mc, 2H), 3.87 (t, J=5.7 Hz, 2H), 7.24 (s, 1H), 7.44-7.50 (m, 3H), 8.33-8.40 (m, 2H). 13C NMR (d6-DMSO, 50.3 MHz, DEPT135): δ=22.66 (+), 38.45 (−), 39.53 (−), 102.22 (Cquart), 106.11 (Cquart), 124.94 (+), 127.65 (+, 2C), 128.09 (+, 2C), 129.53 (Cquart), 138.98 (+), 152.02 (Cquart), 157.15 (Cquart), 159.21 (Cquart), 162.14 (Cquart), 169.47 (Cquart). MS (ES): m/z 339.9 (100) [MH+]. tR(method A)=5.0 min.

Workup

  1. customMeOH is evaporated
  2. dissolutionThe residue is dissolved in 2N NaOH (200 mL)
  3. extractionextracted with Et2O (2×30 mL)
  4. customhas precipitated
  5. customno more solid precipitates)
  6. filtrationThe beige solid is filtered off
  7. customdried

Sources & evidence

ORD record
ord-58ceb429a6374492859856757a2169d9
Source dataset
uspto-grants-2010_01
Patent number
US07645754B2

Reaction notes

Loading…