Ammonia → 4-Amino-6-chloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine

HRID 356646Notes

Reaction equation

HRID 356646 reaction equation
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6](Cl)[N:5]=[C:4]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:3]=1.[NH3:24]>CO>[NH2:24][C:6]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:2]([Cl:1])[N:3]=[C:4]([C:18]2[N:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 105457064,6-Dichloro-5-(2-methoxyphenoxy)-2,2'-bipyrimidine

Product 1

HCID 189389064-Amino-6-chloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.09 g of 4,6-dichloro-5-(2-methoxy-phenoxy)-2,2'-bipyrimidine (EP-A- 0 526 708) were suspended in 75 ml of methanol and 150 ml of ammonia were condensed at 75° C. using a feedpipe. The reaction mixture was left to come to room temperature overnight, concentrated in a water-jet vacuum and the residue was partitioned between a small amount of water and methylene chloride (500 ml). The organic phase was dried over sodium sulphate and concentrated on a rotary evaporator. The residue was triturated with ether, the resulting solid was separated and dried in a high vacuum. The 4-amino-6-chloro-5-(2-methoxy-phenoxy )-2,2'-bipyrimidine was thus obtained as a fine, almost white powder. MS: 329 (M).

Workup

  1. customcondensed at 75° C.
  2. waitThe reaction mixture was left
  3. concentrationconcentrated in a water-jet vacuum
  4. customthe residue was partitioned between a small amount of water and methylene chloride (500 ml)
  5. dry with materialThe organic phase was dried over sodium sulphate
  6. concentrationconcentrated on a rotary evaporator
  7. customThe residue was triturated with ether
  8. customthe resulting solid was separated
  9. customdried in a high vacuum

Sources & evidence

ORD record
ord-6f5b417188e148ba8f69a679e224e9f7
Source dataset
uspto-grants-1998_11
Patent number
US05837708

Reaction notes

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