Methyl iodide → HCID 50941769, compound

HRID 1507775Notes

Reaction equation

HRID 1507775 reaction equation
N[C:2]1N=C(O)C(NC(=O)CCOC2C=CC(F)=CC=2)=C(O)N=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.[NH2:37][C:38]1[N:39]=[C:40]([SH:57])[C:41]2[N:46]=[C:45]([CH2:47][CH2:48][O:49][C:50]3[CH:55]=[CH:54][C:53]([F:56])=[CH:52][CH:51]=3)[S:44][C:42]=2[N:43]=1.C(N(CC)CC)C.IC>N1C=CC=CC=1.CS(C)=O.O>[F:56][C:53]1[CH:54]=[CH:55][C:50]([O:49][CH2:48][CH2:47][C:45]2[S:44][C:42]3[N:43]=[C:38]([NH2:37])[N:39]=[C:40]([S:57][CH3:2])[C:41]=3[N:46]=2)=[CH:51][CH:52]=1

Participants

9

Reactant 5

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 14817Phosphorus sulfide (P2S5)HCID 178508994HCID 178508994, compoundHCID 178509030HCID 178509030, compound

Product 1

HCID 50941769HCID 50941769, compoundYield 21.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

A solution of N-(2-amino-4,6-dihydroxypyrimidin-5-yl)-3-(4-fluorophenoxy)propanamide (2.5 g, 8.11 mmol) and phosphorus pentasulfide (3.60 g, 16.2 mmol) in dry pyridine (40 ml) was refluxed for 6 hours. After cooling down to room temperature, the precipitate was filtered off, washed with ethylacetate and dried. The crude 5-amino-2-(2-(4-fluorophenoxy)ethyl)-thiazolo[5,4-d]pyrimidine-7-thiol (2.0 g, 6.20 mmol) was redissolved in DMSO (30 ml). Triethylamine (0.85 ml, 6.12 mmol) and iodomethane (0.31 ml, 4.90 mmol) were added. The reaction mixture was stirred for 12 hours at room temperature under a nitrogen atmosphere. The mixture was poured into water and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and the solvents were removed under reduced pressure. The crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 100:1), yielding the title compound as a light yellow solid (0.45 g, 15% over 2 steps).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with ethylacetate
  3. customdried
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customthe solvents were removed under reduced pressure
  7. customThe crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 100:1)

Sources & evidence

ORD record
ord-536969c30c9244989263c58add997c8e
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

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