Phosphorus oxychloride → HCID 62178176, compound

HRID 1520339Notes

Reaction equation

HRID 1520339 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9](=O)[C:10]3[CH:15]=[CH:14][S:13][C:11]=3[N:12]=2)[CH:2]=1.N.O.O=P(Cl)(Cl)[Cl:21]>>[Cl:21][C:9]1[C:10]2[CH:15]=[CH:14][S:13][C:11]=2[N:12]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 12896473Azane;hydrateHCID 67298233HCID 67298233, compound

Product 1

HCID 62178176HCID 62178176, compound

Conditions

Temperature
120 °C

Procedure

The suspension of 2-(pyridin-3-yl)thieno[2,3-d]pyrimidin-4(3H)-one (6.0 g, containing salts) in POCl3 (30 ml.) was stirred at 120° C. for 10 h. After the reaction was completed, the mixture was added to ice-water slowly. The pH was adjusted to ˜7 by slowly adding NH3.H2O at 0° C., then a precipitate formed. The solid was collected and 540 mg of 4-chloro-2-(pyridin-3-yl)thieno[2,3-d]pyrimidine was obtained as a brown solid, LCMS m/z=247.9, 250.0 (M+1) (Method B) (retention time=1.85 min).

Workup

  1. customa precipitate formed
  2. customThe solid was collected

Sources & evidence

ORD record
ord-146abc9f4d984f66a4a07367c920c961
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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