Ammonia → HCID 54310262, compound

HRID 442567Notes

Reaction equation

HRID 442567 reaction equation
Cl[C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][N:8]([CH2:12][O:13][CH:14]([OH:18])[CH2:15][CH2:16][OH:17])[C:4]=2[N:5]=[CH:6][N:7]=1.[NH3:19]>>[NH2:19][C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][N:8]([CH2:12][O:13][CH:14]([OH:18])[CH2:15][CH2:16][OH:17])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 53732428HCID 53732428, compound

Product 1

HCID 54310262HCID 54310262, compound

Conditions

Temperature
135 °C

Procedure

Compound 22a was prepared by heating the 4,5-dichloro-7-[(1,3-dihydroxypropoxy)methyl]pyrrolo[2,3-d]pyrimidine with saturated methanolic ammonia (15 mL) in a steel reaction vessel. The vessel was then heated to 135° C. for eight hours after which time the vessel was cooled and the solvent was removed in vacuo at 40° C. The resulting solid was then recrystallized from methanol to yield 0.28 g (61%). mp=175°-176.5° C. 1H NMR (DMSO-d6): δ3.22-3.50 (m, 5), 4.58 (t, 2, exchanges with D2O, OH); 5.57 (s, 2, C-1'); 6.88 (bs, 2, exchanges with D2O, NH2) 7.47 (s, 1, C6), 8.11 (s, 1, C-2). Anal. for C10H13N4O3Cl. (C,H,N).

Workup

  1. temperaturewas cooled
  2. customthe solvent was removed in vacuo at 40° C
  3. customThe resulting solid was then recrystallized from methanol
  4. customto yield 0.28 g (61%)

Sources & evidence

ORD record
ord-145cb62087cc48e6aca1b67027380a67
Source dataset
uspto-grants-1999_04
Patent number
USRE036187

Reaction notes

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