Trimethyl Phosphate → (2-Chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethyl)phosphonic acid dimethyl ester

HRID 2098677Notes

Reaction equation

HRID 2098677 reaction equation
Br[CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([Cl:18])=[N:6][C:5]=2[CH:4]=1.[P:19](OC)([O:23][CH3:24])([O:21][CH3:22])=[O:20]>O>[CH3:22][O:21][P:19]([CH2:2][C:3]1[S:11][C:10]2[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[N:8][C:7]([Cl:18])=[N:6][C:5]=2[CH:4]=1)(=[O:20])[O:23][CH3:24]

Participants

4

Reactant 2

HCID 10541Trimethyl PhosphateHCID 461807264-(6-(Bromomethyl)-2-chlorothieno[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 86618396(2-Chloro-4-morpholin-4-ylthieno[3,2-d]pyrimidin-6-ylmethyl)phosphonic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-bromomethyl-2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 30 from Example 9 (1.0 g) and trimethyl phosphate (5 mL) was heated at reflux for 3 h. After cooling to room temperature, water (20 mL) was added and the product filtered, washed with water and dried under vacuum to give (2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-phosphonic acid dimethyl ester as a yellow solid (0.54 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. filtrationthe product filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-83d80250afba4948a3d6491156332ea0
Source dataset
uspto-grants-2013_05
Patent number
US08450315B2

Reaction notes

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