Formaldehyde → (S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

HRID 1626575Notes

Reaction equation

HRID 1626575 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[C:5]2[CH2:10][N:9]([CH2:11][CH:12]3CC3)[CH2:8][C:6]=2[N:7]=1.C=O.Cl.ClC1N=C(N2CCOC[C@@H]2C)C2CCNCC=2N=1>>[Cl:1][C:2]1[N:3]=[C:4]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@@H:16]2[CH3:21])[C:5]2[CH2:12][CH2:11][N:9]([CH3:10])[CH2:8][C:6]=2[N:7]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 86663153(S)-4-(2-chloro-6-(cyclopropylmethyl)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholineHCID 86663157(S)-4-(2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride

Product 1

HCID 86663156(S)-4-(2-chloro-7-methyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholineYield 78%

Procedure

Method as described for intermediate 8 using formaldehyde (37% solution in water) and (S)-4-(2-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride as starting materials. The mixture was partitioned between saturated NaHCO3 solution and DCM. The organic layer was recovered, dried over MgSO4, filtered and reduced in vacuo, yielding the title compound (2.11 g, 7.47 mmol, 78%).

Workup

  1. customThe mixture was partitioned between saturated NaHCO3 solution and DCM
  2. customThe organic layer was recovered
  3. dry with materialdried over MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-4ddc060b4eca455c9fc74846fd6ef09b
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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