Triethylamine → 5-Methoxy-6-methoxymethyl-4-(2-phenyltetrahydrothiophen-4-ylamino)pyrimidine

HRID 1532958

Reaction equation

HRID 1532958 reaction equation
Cl[C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH2:10][O:11][CH3:12])[N:5]=[CH:4][N:3]=1.[NH2:13][CH:14]1[CH2:18][S:17][CH:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15]1.C1(C2CC(=O)CS2)C=CC=CC=1.C(N(CC)CC)C>O>[CH3:9][O:8][C:7]1[C:2]([NH:13][CH:14]2[CH2:18][S:17][CH:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:15]2)=[N:3][CH:4]=[N:5][C:6]=1[CH2:10][O:11][CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 124137022-Phenyl-4-oxo-tetrahydrothiopheneHCID 152793504-Chloro-5-methoxy-6-(methoxymethyl)pyrimidineHCID 220119364-Amino-2-phenyltetrahydrothiophene

Product 1

HCID 220119465-Methoxy-6-methoxymethyl-4-(2-phenyltetrahydrothiophen-4-ylamino)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

1.6 g (8.5 mmol) of 4-chloro-5-methoxy-6-methoxymethylpyrimidine, 1.5 g (8.5 mmol) of 4-amino-2-phenyltetrahydrothiophene (prepared from 2-phenyl-4-oxo-tetrahydrothiophene (cf. D. N. Reinhard, W. P. Trompenaars, I. Geevers, Synthesis 1978, 368) analogously to the route given in Example B) and 2 ml (14 mmol) of triethylamine were heated for 24 hours at 85° C. After cooling, the mixture was diluted with water and extracted with ether, and the organic phase was washed with saturated NaCl solution. After drying and concentrating, the residue was purified by column chromatography using petroleum ether/ethyl acetate (9:1). This gave 1.18 g (42% of theory) of a pale yellow syrup.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ether
  3. washthe organic phase was washed with saturated NaCl solution
  4. customAfter drying
  5. concentrationconcentrating
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f09260a59f884186b0b403e683e853c8
Source dataset
uspto-grants-2001_03
Patent number
US06207668B1

Linked notes

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