Phosphorus oxychloride → 4-Chloro-5-methylpyrimidin-2-amine

HRID 1524839Notes

Reaction equation

HRID 1524839 reaction equation
[CH3:1][C:2]1[C:7](=O)[NH:6][C:5]([NH2:9])=[N:4][CH:3]=1.O=P(Cl)(Cl)[Cl:12]>>[Cl:12][C:7]1[C:2]([CH3:1])=[CH:3][N:4]=[C:5]([NH2:9])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 852215-Methylisocytosine

Product 1

HCID 5886284-Chloro-5-methylpyrimidin-2-amineYield 29%

Procedure

A mixture of 5-methylisocytosine (3 g, 24.0 mmol) and POCl3 (20 mL) was refluxed for 45 minutes. Excess of POCl3 was removed under reduced pressure and the residue was poured over ice. The resulting mixture was made basic with ammonia at 10° C. The precipitate was filtrated and crystallized from ethanol to give 4-chloro-2-amino-5-methylpyrimidine (1 g 29.0% yield). 1H NMR (400 MHz, DMSO): δ 8.11 (s, 1 H), 6.81 (br s, 2 H), 2.04 (s, 3 H).

Workup

  1. temperaturewas refluxed for 45 minutes
  2. customExcess of POCl3 was removed under reduced pressure
  3. additionthe residue was poured over ice
  4. customwas made basic with ammonia at 10° C
  5. filtrationThe precipitate was filtrated
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-269f14a31bc54511ad7eb53b03fa9042
Source dataset
uspto-grants-2015_07
Patent number
US09079916B2

Reaction notes

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