Hydrochloric Acid → HCID 136337780, compound

HRID 533205Notes

Reaction equation

HRID 533205 reaction equation
C(OC[N:10]1[C:18]2[C:17]([O:19]C(C)(C)C)=[N:16][CH:15]=[N:14][C:13]=2[C:12]([CH2:24][NH:25][C:26]([CH2:31][S:32][CH3:33])([CH2:29][OH:30])[CH2:27][OH:28])=[CH:11]1)C1C=CC=CC=1.Cl>CO>[OH:28][CH2:27][C:26]([NH:25][CH2:24][C:12]1[C:13]2[N:14]=[CH:15][NH:16][C:17](=[O:19])[C:18]=2[NH:10][CH:11]=1)([CH2:31][S:32][CH3:33])[CH2:29][OH:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67222322HCID 67222322, compound

Product 1

HCID 136337780HCID 136337780, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 2-((5-(benzyloxymethyl)-4-tert-butoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methylamino)-2-(methylthiomethyl)propane-1,3-diol (200 mg, 0.421 mmol) in methanol (1 mL) was added to a solution of concentrated hydrochloric acid (2 mL) in methanol (5 mL) and the reaction was heated at 100° C. for 3 h. The contents of the flask were concentrated under reduced pressure, redissolved in methanol (5 mL) and Amberlyst 21 resin (˜1 g) was added. After stirring for 1 h at ambient temperature the resin was removed by filtration, the filtrate concentrated under reduced pressure and then redissolved in 7 M methanolic ammonia (5 mL) and stirred for 30 min. TLC(CH2Cl2:7 M methanolic ammonia, 4:1, visualised with Erlichs) indicated the reaction was complete so the solution was concentrated under reduced pressure and the residue dry-loaded on to a silica column. Purification by flash column chromatography (CH2Cl2:7 M methanolic ammonia, 3:1, visualised with Erlichs) gave 7-((1,3-dihydroxy-2-(methylthiomethyl)propan-2-ylamino)methyl)-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one (62.0 mg, 49%) as a white foam. 1H NMR (D2O, drop of DCl) δ 8.91 (1H), 7.79 (1H), 4.43 (2H), 3.84 (d, J=12.7 Hz, 2H), 3.79 (d, J=12.7 Hz, 2H), 2.92 (s, 2H), 2.13 (s, 3H). 13C NMR (D2O, drop of DCl): δ 152.8, 145.2, 133.3, 131.8, 118.5, 103.5, 67.4, 59.2, 35.4, 33.5, 17.0. +ESMS Found 299.1185 (M+Fr) C12H19N4O3S requires 299.1178.

Workup

  1. concentrationThe contents of the flask were concentrated under reduced pressure
  2. dissolutionredissolved in methanol (5 mL)
  3. additionAmberlyst 21 resin (˜1 g) was added
  4. customwas removed by filtration
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionredissolved in 7 M methanolic ammonia (5 mL)
  7. stirringstirred for 30 min
  8. concentrationwas concentrated under reduced pressure
  9. customPurification by flash column chromatography (CH2Cl2:7 M methanolic ammonia, 3:1, visualised with Erlichs)

Sources & evidence

ORD record
ord-04851f22567347239b3a49792312d9af
Source dataset
uspto-grants-2014_10
Patent number
US08853224B2

Reaction notes

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